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Journal articles on the topic 'Coupling Reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 20 July 2024

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1

Pires, Marina, Sara Purificação, A. Santos, and M. Marques. "The Role of PEG on Pd- and Cu-Catalyzed Cross-Coupling Reactions." Synthesis 49, no. 11 (April 26, 2017): 2337–50. http://dx.doi.org/10.1055/s-0036-1589498.

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Carbon–carbon and carbon–heteroatom coupling reactions are among the most important transformations in organic synthesis as they enable complex structures to be formed from readily available compounds under different routes and conditions. Several metal-catalyzed cross-coupling reactions have been developed creating many efficient methods accessible for the direct formation of new bonds between differently hybridized carbon atoms.During the last decade, much effort has been devoted towards improvement of the sustainability of these reactions, such as catalyst recovery and atom efficiency. Polyethylene glycol (PEG) can be used as a medium, as solid-liquid phase transfer catalyst, or even as a polymer support. PEG has been investigated in a wide variety of cross-coupling reactions either as an alternative solvent to the common organic solvents or as a support for catalyst, substrate, and ligand. In this review we will summarize the different roles of PEG in palladium- and copper-catalyzed cross-coupling reactions, with the focus on Heck, Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig, Stille, Fukuyama, and homocoupling reactions. We will highlight the role of PEG, the preparation of PEGylated catalysts and substrates, and the importance for the reaction outcome and applicability.1 Introduction2 PEG in Heck Reactions3 PEG in Homocoupling Reactions4 PEG in Suzuki–Miyaura Reactions5 PEG in Sonogashira Reactions6 PEG in Buchwald–Hartwig Reactions7 PEG in Stille Reactions8 PEG in Fukuyama Reactions9 PEG in Miscellaneous Cross-Coupling Routes10 Conclusions

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2

Kumar, Anil, Saurav Kumar, Jyoti Jyoti, Deepak Gupta, and Gajendra Singh. "A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview." SynOpen 07, no. 04 (November 2023): 580–614. http://dx.doi.org/10.1055/s-0040-1720096.

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AbstractDuring the previous couple of decades, transition-metal (Fe, Co, Cu, Ni, Ru, Rh, Pd, Ag, Au) catalyzed inter- and intramolecular coupling reactions have attracted huge attention for the construction of C–C and C–heteroatom (like C–N, C–P, C–O, C–S, etc.) bonds to synthesize a diverse range of polymers, fine chemicals, and agrochemicals (mainly fungicides, herbicides, and insecticides), as well as biologically and pharmaceutically important organic molecules. Furthermore, the employment of lower cost and easily available metals such as first-row transition-metal salts or metal complexes of Fe, Co, Cu, Ni as catalysts compared to the precious metals such as Pd, Ag, Au in cross-coupling reactions have led to major advances in applications within the fields of synthesis. A number of cross-coupling reactions catalyzed by transition metals have been explored, including Suzuki, Heck, Sonogashira, Stille, Kumada, Kochi, Murahashi, Corriu, and Negishi reactions, as well as carbonylative, decarboxylative, reactions and α-arylations. In this review, we offer a comprehensive summary of the cross-coupling reaction catalyzed by different transition metals from the year 2009 to date.1 Introduction2 Pd-Catalyzed Reactions2.1 C–C Cross-Coupling Reactions2.2 C–N Cross-Coupling Reactions2.3 C–P Cross-Coupling Reactions3 Ni-Catalyzed Cross-Coupling Reactions3.1 C–C Cross-Coupling Reactions4 Cu-Catalyzed Cross-Coupling Reactions4.1 C–C Cross-Coupling Reactions4.2 C–O Cross-Coupling Reactions4.2 C–N Cross-Coupling Reactions4.4 C–P Cross-Coupling Reactions4.5 C–Se Cross-Coupling Reactions4.6 C–S Cross-Coupling Reactions5 Fe-Catalyzed Reactions5.1 C–C Cross-Coupling Reactions5.2 C–S Cross-Coupling Reactions6 Co-Catalyzed Reactions7 Transition-Metal Nanoparticle-Promoted Reactions7.1 Pd Nanoparticles7.2 Cu Nanoparticles8 Miscellaneous Reactions9 Perspectives and Future Directions

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3

Kotha, Sambasivarao, Milind Meshram, and Nageswara Panguluri. "Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions." Synthesis 51, no. 09 (March 25, 2019): 1913–22. http://dx.doi.org/10.1055/s-0037-1612418.

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We have summarized diverse synthetic approaches for the modification of peptides by employing transition-metal-catalyzed reactions. These methods can deliver unusual peptides suitable for peptidomimetics. To this end, several popular reactions such as Diels–Alder, 1,3-dipolar cycloaddition, [2+2+2] cyclotrimerization, metathesis, Suzuki–Miyaura cross-coupling, and Negishi coupling have been used to assemble modified peptides by post-assembly chemical modification strategies.1 Introduction2 Synthesis of a Cyclic α-Amino Acid Derivative via a Ring-Closing Metathesis Protocol3 Peptide Modification Using a Ring-Closing Metathesis Strategy4 Peptide Modification via a [2+2+2] Cyclotrimerization Reaction5 Peptide Modification by Using [2+2+2] Cyclotrimerization and Suzuki Coupling6 Peptide Modification via a Suzuki–Miyaura Cross-Coupling7 Peptide Modification via Cross-Enyne Metathesis and a Diels–Alder Reaction as Key Steps8 Peptide Modification via 1,3-Dipolar Cycloaddition Reactions9 Modified Peptides via Negishi Coupling10 A Modified Dipeptide via Ethyl Isocyanoacetate11 Conclusions

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4

Daley, Ryan A., and Joseph J. Topczewski. "Aryl-Decarboxylation Reactions Catalyzed by Palladium: Scope and Mechanism." Synthesis 52, no. 03 (December 13, 2019): 365–77. http://dx.doi.org/10.1055/s-0039-1690769.

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Palladium-catalyzed cross-couplings and related reactions have enabled many transformations essential to the synthesis of pharmaceuticals, agrochemicals, and organic materials. A related family of reactions that have received less attention are decarboxylative functionalization reactions. These reactions replace the preformed organometallic precursor (e.g., boronic acid or organostannane) with inexpensive and readily available carboxylic acids for many palladium-catalyzed reactions. This review focuses on catalyzed reactions where the elementary decarboxylation step is thought to occur at a palladium center. This review does not include decarboxylative reactions where decarboxylation is thought to be facilitated by a second metal (copper or silver) and is specifically limited to (hetero)arenecarboxylic acids. This review includes a discussion of oxidative Heck reactions, protodecarboxylation reactions, and cross-coupling reactions among others.1 Introduction2 Oxidative Heck Reactions3 Protodecarboxylation Reactions4 Cross-Coupling Reactions5 Other Reactions6 Conclusion

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5

Lee, Sunwoo, and Muhammad Aliyu Idris. "Recent Advances in Decarboxylative Reactions of Alkynoic Acids." Synthesis 52, no. 16 (April 6, 2020): 2277–98. http://dx.doi.org/10.1055/s-0040-1707600.

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Alkynoic acids have been widely employed as alkyne and alkene sources in decarboxylative reactions. Alkynoic acid coupling leads to the formation of direct coupling products and cyclized products through sequential reactions. Moreover, homocoupling and multicomponent reactions have been developed. The decarboxylative addition of alkynoic acids generates the corresponding alkene products. A number of synthetic methods are utilized for the preparation of arylpropynoic acids including the Sonogashira coupling and the carboxylation of terminal alkynes. Recently, the use of decarboxylative halogenations has also been reported. This review covers decarboxylative reactions of alkynoic acids reported between 2013 and 2019; further, it is divided into several sections according to the type of reaction.1 Introduction2 Direct Coupling3 Sequential Reactions4 Homocoupling5 Multicomponent Reactions6 Addition7 Halogenations8 Synthesis of Alkynoic Acids9 Conclusion

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6

Koóš, Peter, Martin Markovič, Pavol Lopatka, and Tibor Gracza. "Recent Applications of Continuous Flow in Homogeneous Palladium Catalysis." Synthesis 52, no. 23 (August 3, 2020): 3511–29. http://dx.doi.org/10.1055/s-0040-1707212.

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Considerable advances have been made using continuous flow chemistry as an enabling tool in organic synthesis. Consequently, the number of articles reporting continuous flow methods has increased significantly in recent years. This review covers the progress achieved in homogeneous palladium catalysis using continuous flow conditions over the last five years, including C–C/C–N cross-coupling reactions, carbonylations and reductive/oxidative transformations.1 Introduction2 C–C Cross-Coupling Reactions3 C–N Coupling Reactions4 Carbonylation Reactions5 Miscellaneous Reactions6 Key to Schematic Symbols7 Conclusion

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7

Nicholas, Kenneth M., and Chandrasekhar Bandari. "Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides." Synthesis 53, no. 02 (October 7, 2020): 267–78. http://dx.doi.org/10.1055/s-0040-1707269.

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AbstractThe prospective utilization of abundant, CO2-neutral, renewable feedstocks is driving the discovery and development of new reactions that refunctionalize oxygen-rich substrates such as alcohols and polyols through C–O bond activation. In this review, we highlight the development of transition-metal-promoted reactions of renewable alcohols and epoxides that result in carbon–carbon bond-formation. These include reductive self-coupling reactions and cross-coupling reactions of alcohols with alkenes and arene derivatives. Early approaches to reductive couplings employed stoichiometric amounts of low-valent transition-metal reagents to form the corresponding hydrocarbon dimers. More recently, the use of redox-active transition-metal catalysts together with a reductant has enhanced the practical applications and scope of the reductive coupling of alcohols. Inclusion of other reaction partners with alcohols such as unsaturated hydrocarbons and main-group organometallics has further expanded the diversity of carbon skeletons accessible and the potential for applications in chemical synthesis. Catalytic reductive coupling and cross-coupling reactions of epoxides are also highlighted. Mechanistic insights into the means of C–O activation and C–C bond formation, where available, are also highlighted.1 Introduction2 Stoichiometric Reductive Coupling of Alcohols3 Catalytic Reductive Coupling of Alcohols3.1 Heterogeneous Catalysis3.2 Homogeneous Catalysis4 Reductive Cross-Coupling of Alcohols4.1 Reductive Alkylation4.2 Reductive Addition to Olefins5 Epoxide Reductive Coupling Reactions6 Conclusions and Future Directions

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8

Akkarasamiyo, Sunisa, Somsak Ruchirawat, Poonsaksi Ploypradith, and Joseph S. M. Samec. "Transition-Metal-Catalyzed Suzuki–Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols." Synthesis 52, no. 05 (January 7, 2020): 645–59. http://dx.doi.org/10.1055/s-0039-1690740.

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The Suzuki–Miyaura reaction is one of the most powerful tools for the formation of carbon–carbon bonds in organic synthesis. The utilization of alcohols in this powerful reaction is a challenging task. This short review covers progress in the transition-metal-catalyzed Suzuki–Miyaura-type cross-coupling reaction of π-activated alcohol, such as aryl, benzylic, allylic, propargylic and allenic alcohols, between 2000 and June 2019.1 Introduction2 Suzuki–Miyaura Cross-Coupling Reactions of Aryl Alcohols2.1 One-Pot Reactions with Pre-activation of the C–O Bond2.1.1 Palladium Catalysis2.1.2 Nickel Catalysis2.2 Direct Activation of the C–O Bond2.2.1 Nickel Catalysis3 Suzuki–Miyaura-Type Cross-Coupling Reactions of Benzylic Alcohols4 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allylic Alcohols4.1 Rhodium Catalysis4.2 Palladium Catalysis4.3 Nickel Catalysis4.4 Stereospecific Reactions4.5 Stereoselective Reactions4.6 Domino Reactions5 Suzuki–Miyaura-Type Cross-Coupling Reactions of Propargylic Alcohols5.1 Palladium Catalysis5.2 Rhodium Catalysis6 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allenic Alcohols6.1 Palladium Catalysis6.2 Rhodium Catalysis7 Conclusions

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9

Morimoto, Koji, Toshifumi Dohi, and Yasuyuki Kita. "Metal-free Oxidative Cross-Coupling Reaction of Aromatic Compounds Containing Heteroatoms." Synlett 28, no. 14 (June 21, 2017): 1680–94. http://dx.doi.org/10.1055/s-0036-1588455.

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The biaryl unit containing a heteroatom is a key structure in a large number of natural products and π-conjugated organic systems. The cross-couplings can provide powerful methods for the construction of biaryls and heterobiaryls; thus the development of a new coupling method has been intensively studied by synthetic chemists. Therefore, the oxidative biaryl coupling reaction of arenes containing a heteroatom is a significantly attractive, convenient, and straightforward route to the synthesis of biaryls due to its operational simplicity avoiding the preparation of the corresponding halogenated and metallated arenes. In this report, recent progress in the field of metal-free oxidative cross-coupling reactions of aromatic compounds using hypervalent iodine(III) reagents, is presented.1 Introduction2 Cyanation and Halogenation Reactions of Heteroaromatic Compounds3 Biaryl Coupling Reaction of Heteroaromatic Compounds3.1 Regioselective Coupling Reaction of Thiophenes3.2 Cross-Coupling Reaction of Thiophenes3.3 Coupling Reaction of EDOT and Pyrroles3.4 Cross-Coupling Reaction of Pyrroles4 Cross-Coupling Reaction of Anilines5 Cross-Coupling Reaction of Phenols6 Cross-Coupling Reaction of N-Heteroaromatics with Aryl Radicals from Diaryliodonium(III) Salts7 Conclusion

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10

Wang, Lei, Jincan Yan, Pinhua Li, Min Wang, and Caina Su. "The effects of amines on oxidative homo-coupling of terminal alkynes promoted by copper salts." Journal of Chemical Research 2005, no. 2 (February 2005): 112–15. http://dx.doi.org/10.3184/0308234054497083.

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The effects of all kinds of amines on homo-couplings (Glaser reactions) of terminal alkynes promoted by copper salts and the Sonogashira coupling reactions were studied systematically. Diethylamine (2° amine) can serve as an excellent solvent, base and coordination ligand in the oxidative homo-coupling of terminal alkynes and several modified Glaser coupling procedures have been developed which are based on a catalytic amount of cuprous salts (CuI, CuBr or CuCl) with diethylamine systems. Homo-coupling of terminal acetylenes in the Sonogashira reaction could be inhibited by using triethylamine (3° amine) as reaction medium, and the cross-coupling products were formed as the exclusive products.

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11

Larson, Gerald. "Some Aspects of the Chemistry of Alkynylsilanes." Synthesis 50, no. 13 (May 18, 2018): 2433–62. http://dx.doi.org/10.1055/s-0036-1591979.

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In amongst the considerable chemistry of acetylenes there lies some unique chemistry of alkynylsilanes (silylacetylenes) some of which is reviewed herein. This unique character is exemplified not only in the silyl protection of the terminal C–H of acetylenes, but also in the ability of the silyl group to be converted into other functionalities after reaction of the alkynylsilane and to its ability to dictate and improve the regioselectivity of reactions at the triple bond. This, when combined with the possible subsequent transformations of the silyl group, makes their chemistry highly versatile and useful.1 Introduction2 Safety3 Synthesis4 Protiodesilylation5 Sonogashira Reactions6 Cross-Coupling with the C–Si Bond7 Stille Cross-Coupling8 Reactions at the Terminal Carbon9 Cross-Coupling with Silylethynylmagnesium Bromides10 Reactions of Haloethynylsilanes11 Cycloaddition Reactions11.1 Formation of Aromatic Rings11.2 Diels–Alder Cyclizations11.3 Formation of Heterocycles11.4 Formation of 1,2,3-Triazines11.5 [2+3] Cycloadditions11.6 Other Cycloadditions12 Additions to the C≡C Bond13 Reactions at the C–Si Bond14 Miscellaneous Reactions

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12

Staubitz, Anne, Melanie Walther, Waldemar Kipke, Sven Schultzke, and Souvik Ghosh. "Modification of Azobenzenes by Cross-Coupling Reactions." Synthesis 53, no. 07 (January 28, 2021): 1213–28. http://dx.doi.org/10.1055/s-0040-1705999.

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AbstractAzobenzenes are among the most extensively used molecular switches for many different applications. The need to tailor them to the required task often requires further functionalization. Cross-coupling reactions are ideally suited for late-stage modifications. This review provides an overview of recent developments in the modification of azobenzene and its derivatives by cross-coupling reactions.1 Introduction2 Azobenzenes as Formally Electrophilic Components2.1 Palladium Catalysis2.2 Nickel Catalysis2.3 Copper Catalysis2.4 Cobalt Catalysis3 Azobenzenes as Formally Nucleophilic Components3.1 Palladium Catalysis3.2 Copper Catalysis3.3 C–H Activation Reactions4 Azobenzenes as Ligands in Catalysts5 Diazocines5.1 Synthesis5.2 Cross-Coupling Reactions6 Conclusion

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13

SUZUKI, Akira. "Organoborane coupling reactions (Suzuki coupling)." Proceedings of the Japan Academy, Series B 80, no. 8 (2004): 359–71. http://dx.doi.org/10.2183/pjab.80.359.

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14

Bhavsar, Nirav, Vivaksha Patel, and Manish Misra. "Effect of Reaction Conditions on the Conversion and Selectivity of MCM-41 and Al-20-MCM-41 Catalyzed Amine Coupling Reactions." Asian Journal of Chemistry 34, no. 11 (2022): 2929–34. http://dx.doi.org/10.14233/ajchem.2022.23921.

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The study has been performed to examine the effect of different reaction conditions (presence of a solvent, absence of solvent, presence of air and closed vessel with an absence of air) on the conversion and selectivity of oxidative coupling reactions of amines to imines using MCM-41 and Al-20-MCM- 41 catalysts. Two types of coupling reactions were discussed viz. self-coupling and cross coupling. Self-coupling reaction was observed to be faster with Al-20-MCM-41 than MCM-41, while the cross-coupling reactions with Al-20-MCM-41 was slightly slower than MCM-41. The conversion and selectivity of self and cross coupling reactions in different reaction conditions were also investigated. The reaction was found to be of shifting order, initially first order when amine concentration was high and tending towards zero at lower amine concentration. It was evident that both catalysts Al-20-MCM-41 and MCM-41 showed a good catalytic activity on the oxidative coupling reactions of amine but somewhat higher conversion was obtained with Al-20-MCM-41 because of presence of acidic site.

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Vaaland, Ingrid Caroline, and Magne Olav Sydnes. "Consecutive Palladium Catalyzed Reactions in One-Pot Reactions." Mini-Reviews in Organic Chemistry 17, no. 5 (August 11, 2020): 559–69. http://dx.doi.org/10.2174/1570193x16666190716150048.

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Combining palladium catalyzed reactions in one-pot reactions represents an efficient and economical use of catalyst. The Suzuki-Miyaura cross-coupling has been proven to be a reaction which can be combined with other palladium catalyzed reactions in the same pot. This mini-review will highlight some of the latest examples where Suzuki-Miyaura cross-coupling reactions have been combined with other palladium catalyzed reactions in one-pot reaction. Predominantly, examples with homogeneous reaction conditions will be discussed in addition to a few examples from the authors where Pd/C have been used as a catalyst.

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16

Bolm, Carsten. "Cross-Coupling Reactions." Journal of Organic Chemistry 77, no. 12 (June 15, 2012): 5221–23. http://dx.doi.org/10.1021/jo301069c.

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17

Bolm, Carsten. "Cross-Coupling Reactions." Organic Letters 14, no. 12 (June 15, 2012): 2925–28. http://dx.doi.org/10.1021/ol301436v.

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18

Goossen, Lukas J., Florence Collet, and Käthe Goossen. "Decarboxylative Coupling Reactions." Israel Journal of Chemistry 50, no. 5-6 (December 2010): 617–29. http://dx.doi.org/10.1002/ijch.201000039.

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19

Odell, Luke, Mats Larhed, and Linda Åkerbladh. "Palladium-Catalyzed Molybdenum Hexacarbonyl-Mediated Gas-Free Carbonylative Reactions." Synlett 30, no. 02 (October 2, 2018): 141–55. http://dx.doi.org/10.1055/s-0037-1610294.

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This account summarizes Pd(0)-catalyzed Mo(CO)6-mediated gas-free carbonylative reactions published in the period October 2011 to May 2018. Presented reactions include inter- and intramolecular carbonylations, carbonylative cross-couplings, and carbonylative multicomponent reactions using Mo(CO)6 as a solid source of CO. The presented methodologies were developed mainly for small-scale applications, avoiding the problematic use of gaseous CO in a standard laboratory. In most cases, the reported Mo(CO)6-mediated carbonylations were conducted in sealed vials or by using two-chamber solutions.1 Introduction2 Recent Developments2.1 New CO Sources2.2 Two-Chamber System for ex Situ CO Generation2.3 Multicomponent Carbonylations3 Carbonylations with N and O Nucleophiles4 Carbonylative Cross-Coupling Reactions with Organometallics5 Carbonylative Cascade Reactions6 Carbonylative Cascade, Multistep Reactions7 Summary and Outlook

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20

Teichert, Johannes F., and Lea T. Brechmann. "Catch It If You Can: Copper-Catalyzed (Transfer) Hydrogenation Reactions and Coupling Reactions by Intercepting Reactive Intermediates Thereof." Synthesis 52, no. 17 (July 13, 2020): 2483–96. http://dx.doi.org/10.1055/s-0040-1707185.

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The key reactive intermediate of copper(I)-catalyzed alkyne semihydrogenations is a vinylcopper(I) complex. This intermediate can be exploited as a starting point for a variety of trapping reactions. In this manner, an alkyne semihydrogenation can be turned into a dihydrogen-mediated coupling reaction. Therefore, the development of copper-catalyzed (transfer) hydrogenation reactions is closely intertwined with the corresponding reductive trapping reactions. This short review highlights and conceptualizes the results in this area so far, with H2-mediated carbon–carbon and carbon–heteroatom bond-forming reactions emerging under both a transfer hydrogenation setting as well as with the direct use of H2. In all cases, highly selective catalysts are required that give rise to atom-economic multicomponent coupling reactions with rapidly rising molecular complexity. The coupling reactions are put into perspective by presenting the corresponding (transfer) hydrogenation processes first.1 Introduction: H2-Mediated C–C Bond-Forming Reactions2 Accessing Copper(I) Hydride Complexes as Key Reagents for Coupling Reactions; Requirements for Successful Trapping Reactions 3 Homogeneous Copper-Catalyzed Transfer Hydrogenations4 Trapping of Reactive Intermediates of Alkyne Transfer Semihydrogenation Reactions: First Steps Towards Hydrogenative Alkyne Functionalizations 5 Copper(I)-Catalyzed Alkyne Semihydrogenations6 Copper(I)-Catalyzed H2-Mediated Alkyne Functionalizations; Trapping of Reactive Intermediates from Catalytic Hydrogenations6.1 A Detour: Copper(I)-Catalyzed Allylic Reductions, Catalytic Generation of Hydride Nucleophiles from H2 6.2 Trapping with Allylic Electrophiles: A Copper(I)-Catalyzed Hydroallylation Reaction of Alkynes 6.3 Trapping with Aryl Iodides7 Conclusion

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21

Ji, Yuan, Ning Zhong, Zinan Kang, Guobing Yan, and Ming Zhao. "Synthesis of Internal Alkynes through an Effective Tandem Elimination–Hydrodebromination–Cross-Coupling of gem-Dibromoalkenes with Halobenzenes." Synlett 29, no. 02 (September 14, 2017): 209–14. http://dx.doi.org/10.1055/s-0036-1590907.

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Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

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Deng, Yu-Hua, Zhihui Shao, and Hui Wang. "An Update of N-Tosylhydrazones: Versatile Reagents for Metal-Catalyzed and Metal-Free Coupling Reactions." Synthesis 50, no. 12 (May 23, 2018): 2281–306. http://dx.doi.org/10.1055/s-0036-1591993.

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N-Tosylhydrazones have had widespread application in organic synthesis for more than a half century. In most of cases, N-tosylhydrazones, as masked diazo compounds, have been generally used in a series of important carbon–carbon and carbon–heteroatom bond-forming reactions. This review provides an update on progress in diverse coupling reactions of N-tosylhydrazones since 2012. The examples selected are mainly categorized by metal-catalyzed and metal-free systems, wherein four main types of transformations including insertion, olefination, alkynylation, and cyclization are discussed for each system.1 Introduction2 Transition-Metal-Catalyzed Coupling Reactions3 Metal-Free Coupling Reactions4 Conclusion and Outlook

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23

Barde, E., A. Guérinot, and J. Cossy. "α-Arylation of Amides from α-Halo Amides Using Metal-Catalyzed Cross-Coupling Reactions." Synthesis 51, no. 01 (December 7, 2018): 178–84. http://dx.doi.org/10.1055/s-0037-1611358.

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Metal-catalyzed α-arylation of amides from α-halo amides with organometallic reagents is reviewed. The article includes Suzuki–Miyaura, Kumada–Corriu, Negishi, and Hiyama cross-coupling reactions.1 Introduction2 Suzuki–Miyaura Cross-Coupling2.1 Palladium Catalysis2.2 Nickel Catalysis3 Kumada–Corriu Cross-Coupling3.1 Nickel Catalysis3.2 Iron Catalysis3.3 Cobalt Catalysis4 Negishi Cross-Coupling5 Hiyama Cross-Coupling6 Conclusion

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Neufeldt, Sharon R., and John E. A. Russell. "C–O-Selective Cross-Coupling of Chlorinated Phenol Derivatives." Synlett 32, no. 15 (May 8, 2021): 1484–91. http://dx.doi.org/10.1055/a-1503-6330.

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AbstractChemoselective cross-coupling of phenol derivatives is valuable for generating products that retain halides. Here we discuss recent developments in selective cross-couplings of chloroaryl phenol derivatives, with a particular focus on reactions of chloroaryl tosylates. The first example of a C–O-selective Ni-catalyzed Suzuki–Miyaura coupling of chloroaryl tosylates is discussed in detail.1 Introduction2 Density Functional Theory Studies on Oxidative Addition at Nickel(0)3 Stoichiometric Oxidative Addition Studies4 Development of a Tosylate-Selective Suzuki Coupling5 Conclusion and Outlook

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Andrade, Marta A., and Luísa M. D. R. S. Martins. "New Trends in C–C Cross-Coupling Reactions: The Use of Unconventional Conditions." Molecules 25, no. 23 (November 24, 2020): 5506. http://dx.doi.org/10.3390/molecules25235506.

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The ever-growing interest in the cross-coupling reaction and its applications has increased exponentially in the last decade, owing to its efficiency and effectiveness. Transition metal-mediated cross-couplings reactions, such as Suzuki–Miyaura, Sonogashira, Heck, and others, are powerful tools for carbon–carbon bond formations and have become truly fundamental routes in catalysis, among other fields. Various greener strategies have emerged in recent years, given the widespread popularity of these important reactions. The present review comprises literature from 2015 onward covering the implementation of unconventional methodologies in carbon–carbon (C–C) cross-coupling reactions that embodies a variety of strategies, from the use of alternative energy sources to solvent- free and green media protocols.

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Tobrman, Tomáš. "Vinyl Esters and Vinyl Sulfonates as Green Alternatives to Vinyl Bromide for the Synthesis of Monosubstituted Alkenes via Transition-Metal-Catalyzed Reactions." Chemistry 5, no. 4 (October 20, 2023): 2288–321. http://dx.doi.org/10.3390/chemistry5040153.

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This review summarizes the applications of vinyl sulfonate and vinyl acetate as green alternatives for vinyl bromide in cross-coupling reactions. In the first part, the preparation of vinyl sulfonates and their cross-coupling reactions are briefly discussed. Then, a brief review of vinyl acetate cross-coupling reactions, including cyclization reactions, the Fujiware–Moritani reaction, and transvinylation reactions are described.

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Hrizi, Asma, Manon Cailler, Moufida Romdhani-Younes, Yvan Carcenac, and Jérôme Thibonnet. "Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions." Molecules 26, no. 17 (August 31, 2021): 5287. http://dx.doi.org/10.3390/molecules26175287.

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An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.

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Li, Gao, and Rongchao Jin. "Catalysis by gold nanoparticles: carbon-carbon coupling reactions." Nanotechnology Reviews 2, no. 5 (October 1, 2013): 529–45. http://dx.doi.org/10.1515/ntrev-2013-0020.

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AbstractGold nanoparticles have been demonstrated to be efficient catalysts for a wide range of reactions in the past decades, such as oxidation and hydrogenation. In recent research, gold nanoparticle catalysts have been utilized in carbon-carbon coupling reactions. These coupling reactions have been established as convenient and general approaches toward biaryl or propargylamines, which are biologically active compounds, natural products, and pharmaceutical organic compounds. This review aims to highlight the current achievements in the field of gold nanoparticle-catalyzed coupling reactions, including Ullmann homocoupling of halides, oxidative homocoupling of organoboronates, Suzuki cross-coupling of phenylboronic acid and halides, Sonogashira cross-coupling of iodobenzene and phenylacetylene, and A3-coupling reaction of phenylacetylene, amines, and aryl or alkyl aldehydes. The catalytic mechanisms of these carbon-carbon coupling reactions are discussed. Finally, we provide our perspectives on some future work on gold nanocatalysis in coupling reactions.

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Dong, Zhi-Bing, and Jin-Quan Chen. "Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions." Synthesis 52, no. 24 (November 4, 2020): 3714–34. http://dx.doi.org/10.1055/s-0040-1706550.

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AbstractOrganometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the development of novel organometallic reagents, this review draws extensively from their work in this area in recent years.Introduction1 Transition-Metal-Catalyzed Cross Couplings Involving Organozinc Reagents2 Transition-Metal-Catalyzed Cross Couplings Involving Organomagnesium Reagents3 Transition-Metal-Free Cross Couplings Involving Zn and Mg Organometallic Reagents4 Nucleophilic Additions Involving Zn and Mg Organometallic Reagents5 Cross-Coupling Reactions or Nucleophilic Additions Involving Mn, Al-, La-, Li-, Sm- and In-Organometallics6 Conclusion

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Shu, Xing-Zhong, Xiaobo Pang, and Xuejing Peng. "Reductive Cross-Coupling of Vinyl Electrophiles." Synthesis 52, no. 24 (August 11, 2020): 3751–63. http://dx.doi.org/10.1055/s-0040-1707342.

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The synthesis of alkenes (olefins) is a central subject in the synthetic community. The transition-metal-catalyzed reductive cross-coupling of vinyl electrophiles has emerged as a promising tool to produce alkenes with improved flexibility, structural complexity, and functionality tolerance. In this review, we summarized the progress in this field with respect to cross-electrophile couplings and reductive Heck reactions using vinyl electrophiles.1 Introduction2 Cross-Electrophile Coupling of Vinyl Electrophiles3 Reductive Heck Reaction of Vinyl Electrophiles4 Summary and Outlook

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Zhang, Yan, and Bainian Feng. "Asymmetric Catalytic Carbon-Carbon Coupling Reactions via Cross-Dehydrogenative Coupling Reactions." Chinese Journal of Organic Chemistry 34, no. 12 (2014): 2406. http://dx.doi.org/10.6023/cjoc201408030.

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32

Khomenko, Elena. "Spin-Orbit Coupling Effects in BrO- and HOBr Photodissociation Reactions." Chemistry & Chemical Technology 8, no. 2 (June 25, 2014): 117–21. http://dx.doi.org/10.23939/chcht08.02.117.

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33

Christoffers, Jens, and David Kieslich. "Cyanide Anions as Nucleophilic Catalysts in Organic Synthesis." Synthesis 53, no. 19 (May 5, 2021): 3485–96. http://dx.doi.org/10.1055/a-1499-8943.

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AbstractThe nucleophilic addition of a cyanide anion to a carbonyl group is the basis for several cyanide-catalyzed organic reactions, which are summarized in this review. Since cyanide is also a good leaving group, it is an excellent catalyst for transacylation reactions. As an electron-withdrawing group, it also stabilizes a negative charge in its α-position, thus allowing the umpolung of aldehydes to formyl anion equivalents. The two leading examples are the benzoin condensation and the Michael–Stetter reaction furnishing α-hydroxy ketones and 1,4-dicarbonyl compounds, which are both catalyzed by cyanides. The review also covers variants like the silyl-benzoin coupling, the aldimine coupling and the imino-Stetter reaction. Moreover, some cyanide-catalyzed heterocyclic syntheses are reviewed.1 Introduction2 Nucleophilic Additions2.1 Cyanohydrin Formation2.2 Corey–Gilman–Ganem and Related Oxidation Reactions2.3 Conjugate Addition2.4 Intramolecular Carbocyanation3 Transacylation Reactions3.1 Ester Hydrolysis and Transesterification3.2 Formation of Amides3.3 Ketones from Esters3.4 Esters from Ketones4 Transformations Involving an Umpolung4.1 Benzoin Condensation4.2 Aldimine Coupling4.3 Michael–Stetter Reaction4.4 Imino-Stetter Reaction5 Formation of Heterocycles5.1 Oxazolines from Isocyanoacetates5.2 Imidazoles from TosMIC via Oxazolines5.3 Bargellini Reaction6 Conclusion

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Liu, Xingpeng, Heping Huang, Linsen Yang, and Kama Huang. "Degree of Coupling in Microwave-Heating Polar-Molecule Reactions." Molecules 28, no. 3 (January 31, 2023): 1364. http://dx.doi.org/10.3390/molecules28031364.

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Microwave-assisted chemical reactions have been widely used, but the overheating effect limits further applications. The aim of this paper is to investigate the coupling degree of the electromagnetic field and thermal field in microwave-heating chemical reactions whose polarization changes as the reactions proceed. First, the entropy-balance equation of microwave-heating polar-molecule reactions is obtained. Then, the coupling degree of the electromagnetic field and the thermal field in microwave-heating polar-molecule reactions is derived, according to the entropy-balance equation. Finally, the effects of reaction processes on the degree of coupling are discussed. When the time scale of the component-concentration variation is much greater than the wave period during the chemical processes, the degree of coupling is sufficiently small, and the electric and thermal fields are considered as weakly coupled. On the other hand, the degree of coupling may change during the reactions. If the absolute value of the coupling degree becomes larger, due to the change in component concentration, this will lead to a transition from weak coupling to strong coupling.

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35

Ishida, Tamao, Makoto Tokunaga, Zhenzhong Zhang, Haruno Murayama, and Eiji Yamamoto. "C–H Bond Functionalization Using Pd- and Au-Supported Catalysts with Mechanistic Insights of the Active Species." Synthesis 53, no. 18 (March 26, 2021): 3279–89. http://dx.doi.org/10.1055/a-1468-1455.

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AbstractThe process of C–H functionalization has been extensively studied as a direct C–C bond-forming reaction with high atomic efficiency. Efforts have also been made on such reactions by using supported catalysts, which are superior in terms of catalyst separation from the reaction mixture and reusability. In this review, an overview of C–H functionalization reactions, especially those involving Pd- and Au-supported catalysts, is presented. In particular, we discuss reaction mechanisms, active species, leaching, reusability, etc.1 Introduction2 Types of Supported Metal Catalysts and Their Active Species3 Modes of C–H Bond Activation4 Oxidative C–H C–H Coupling of Aryl Compounds5 C–H C–H Coupling Where One Side Is Aromatic6 C–H Acylation of Aromatic Compounds and Related Reactions7 Conclusion

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Lumb, Jean-Philip, and Kenneth Esguerra. "Cu(III)-Mediated Aerobic Oxidations." Synthesis 51, no. 02 (December 3, 2018): 334–58. http://dx.doi.org/10.1055/s-0037-1609635.

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CuIII species have been invoked in many copper-catalyzed transformations including cross-coupling reactions and oxidation reactions. In this review, we will discuss seminal discoveries that have advanced our understanding of the CuI/CuIII redox cycle in the context of C–C and C–heteroatom aerobic cross-coupling reactions, as well as C–H oxidation reactions mediated by CuIII–dioxygen adducts.1 General Introduction2 Early Examples of CuIII Complexes3 Aerobic CuIII-Mediated Carbon–Heteroatom Bond-Forming Reactions4 Aerobic CuIII-Mediated Carbon–Carbon Bond-Forming Reactions5 Bioinorganic Studies of CuIII Complexes from CuI and O2 5.1 O2 Activation5.2 Biomimetic CuIII Complexes from CuI and Dioxygen5.2.1 Type-3 Copper Enzymes and Dinuclear Cu Model Complexes5.2.2 Particulate Methane Monooxygenase and Di- and Trinuclear Cu Model Complexes5.2.3 Dopamine–β-Monooxygenase and Mononuclear Cu Model Complexes6 Conclusion

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Hoffmann, Eufrozina A., and István Nagypál. "Response Reactions: Equilibrium Coupling." Journal of Physical Chemistry B 110, no. 21 (June 2006): 10581–84. http://dx.doi.org/10.1021/jp060951k.

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38

Miller, Scott J., and Christopher D. Bayne. "Diastereoselective Enolsilane Coupling Reactions." Journal of Organic Chemistry 62, no. 17 (August 1997): 5680–81. http://dx.doi.org/10.1021/jo971050y.

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39

Kubota, Koji, and Hajime Ito. "Mechanochemical Cross-Coupling Reactions." Trends in Chemistry 2, no. 12 (December 2020): 1066–81. http://dx.doi.org/10.1016/j.trechm.2020.09.006.

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40

Fu, Hua, and Honghua Rao. "Copper-Catalyzed Coupling Reactions." Synlett 2011, no. 06 (March 16, 2011): 745–69. http://dx.doi.org/10.1055/s-0030-1259919.

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41

Weibel, Jean-Marc, Aurélien Blanc, and Patrick Pale. "Ag-Mediated Reactions: Coupling and Heterocyclization Reactions." Chemical Reviews 108, no. 8 (August 2008): 3149–73. http://dx.doi.org/10.1021/cr078365q.

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42

Cooper, Alasdair K., Paul M. Burton, and David J. Nelson. "Nickel versus Palladium in Cross-Coupling Catalysis: On the Role of Substrate Coordination to Zerovalent Metal Complexes." Synthesis 52, no. 04 (December 19, 2019): 565–73. http://dx.doi.org/10.1055/s-0039-1690045.

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A detailed comparison of the effect of coordinating functional groups on the performance of Suzuki–Miyaura reactions catalysed by nickel and palladium is reported, using competition experiments, robustness screening, and density functional theory calculations. Nickel can interact with a variety of functional groups, which manifests as selectivity in competitive cross-coupling reactions. The presence of these functional groups on exogenous additives has effects on cross-coupling reactions that range from a slight improvement in yield to the complete cessation of the reaction. In contrast, palladium does not interact sufficiently strongly with these functional groups to induce selectivity in cross-coupling reactions; the selectivity of palladium-catalysed cross-coupling reactions is predominantly governed by aryl halide electronic properties.

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43

Ramazani, Ali, Hamideh Ahankar, Zahra T. Nafeh, and Sang W. Joo. "Modern Catalysts in A3- Coupling Reactions." Current Organic Chemistry 23, no. 25 (January 14, 2020): 2783–801. http://dx.doi.org/10.2174/1385272823666191113160643.

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: Propargylamines are an important constituent of diverse, biologically active and industrially valuable compounds. These useful, convenient and effective compounds can be synthesized via the A3-coupling reactions between an aldehyde, amine, and alkyne in the presence of a catalyst. In the past years, most of the catalysts containing transition metals were applied in these reactions, but today, various heterogeneous catalysts, especially nanocatalysts are used. The purpose of this review was to introduce some modern catalysts for the A3-coupling reaction.

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44

Sydnes, Magne O. "Green Bio-Based Solvents in C-C Cross-Coupling Reactions." Current Green Chemistry 6, no. 2 (October 25, 2019): 96–104. http://dx.doi.org/10.2174/2213346106666190411151447.

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Solvent accounts for majority of the waste derived from synthetic transformations. This implies that by making changes to the solvent used by either switching to greener options, reducing the volume of solvent used, or even better avoiding the use of solvent totally will have a positive impact on the environment. Herein, the focus will be on the use of bio-based-green-solvents in C-C crosscoupling reactions highlighting the recent developments in this field of research. Emphasis in this review will be placed on developments obtained for Mizoroki-Heck, Hiyama, Stille, and Suzuki- Miyaura cross-couplings. For these cross-coupling reactions, good reaction conditions utilizing green solvents are now available.

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DaBell, Peter, and Stephen P. Thomas. "Iron Catalysis in Target Synthesis." Synthesis 52, no. 07 (February 5, 2020): 949–63. http://dx.doi.org/10.1055/s-0039-1690813.

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The use of iron-catalysed organic transformations in the total syntheses of natural products has increased significantly. Iron-catalysed cross-coupling reactions are now widely applied in total syntheses and many other transformations, such as alkene functionalisation, oxidation, and cyclisation. The development of these processes, as well as many examples of their use in target synthesis, is presented here.1 Introduction2 Cross-Coupling Reactions3 Functionalisation of Unactivated Alkenes4 Carbocyclisation Reactions5 Oxidations6 Further Examples7 Conclusions

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Hammann, Jeffrey, Maximilian Hofmayer, Ferdinand Lutter, Lucie Thomas, and Paul Knochel. "Recent Advances in Cobalt-Catalyzed Csp2 and Csp3 Cross-Couplings." Synthesis 49, no. 17 (May 29, 2017): 3887–94. http://dx.doi.org/10.1055/s-0036-1588430.

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The present short review article highlights recent progress in the field of transition-metal catalysis. An overview on recent work involving cobalt-catalyzed cross-coupling reactions and some recent advances from our laboratories are given.1 Introduction2 Csp2–Csp2 Cobalt-Catalyzed Cross-Couplings3 Csp2–Csp3 Cobalt-Catalyzed Cross-Couplings4 Conclusion

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47

Steven, Alan. "Micelle-Mediated Chemistry in Water for the Synthesis of Drug Candidates." Synthesis 51, no. 13 (May 21, 2019): 2632–47. http://dx.doi.org/10.1055/s-0037-1610714.

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Micellar reaction conditions, in a predominantly aqueous medium, have been developed for transformations commonly used by synthetic chemists working in the pharmaceutical industry to discover and develop drug candidates. The reactions covered in this review are the Suzuki–Miyaura, Miyaura borylation, Sonogashira coupling, transition-metal-catalysed CAr–N coupling, SNAr, amidation, and nitro reduction. Pharmaceutically relevant examples of these applications will be used to show how micellar conditions can offer advantages in yield, operational ease, amount of waste generated, transition-metal catalyst loading, and safety over the use of organic solvents, irrespective of the setting in which they are used.1 Introduction2 Micelles as Solubilising Agents3 Micelles as Nanoreactors4 Designer Surfactants5 A Critical Evaluation of the Case for Chemistry in Micelles6 Scope of Review7 Suzuki–Miyaura Coupling8 Miyaura Borylation9 Sonogashira Coupling10 Transition-Metal-Catalysed CAr–N Couplings11 SNAr12 Amidation13 Nitro Reduction14 Micellar Sequences15 Summary and Outlook

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Li, Chao-Jun, Jianlin Huang, Xi-Jie Dai, Haining Wang, Ning Chen, Wei Wei, Huiying Zeng, et al. "An Old Dog with New Tricks: Enjoin Wolff–Kishner Reduction for Alcohol Deoxygenation and C–C Bond Formations." Synlett 30, no. 13 (June 13, 2019): 1508–24. http://dx.doi.org/10.1055/s-0037-1611853.

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The Wolff–Kishner reduction, discovered in the early 1910s, is a fundamental and effective tool to convert carbonyls into methylenes via deoxygenation under strongly basic conditions. For over a century, numerous valuable chemical products have been synthesized by this classical method. The reaction proceeds via the reversible formation of hydrazone followed by deprotonation with the strong base to give an N-anionic intermediate, which affords the deoxygenation product upon denitrogenation and protonation. By examining the mechanistic pathway of this century old classical carbonyl deoxygenation, we envisioned and subsequently developed two unprecedented new types of chemical transformations: a) alcohol deoxygenation and b) C–C bond formations with various electrophiles including Grignard-type reaction, conjugate addition, olefination, and diverse cross-coupling reactions.1 Introduction2 Background3 Alcohol Deoxygenation3.1 Ir-Catalyzed Alcohol Deoxygenation3.2 Ru-Catalyzed Alcohol Deoxygenation3.3 Mn-Catalyzed Alcohol Deoxygenation4 Grignard-Type Reactions4.1 Ru-Catalyzed Addition of Hydrazones with Aldehydes and Ketones4.2 Ru-Catalyzed Addition of Hydrazone with Imines4.3 Ru-Catalyzed Addition of Hydrazone with CO2 4.4 Fe-Catalyzed Addition of Hydrazones5 Conjugate Addition Reactions5.1 Ru-Catalyzed Conjugate Addition Reactions5.2 Fe-Catalyzed Conjugate Addition Reactions6 Cross-Coupling Reactions6.1 Ni-Catalyzed Negishi-type Coupling6.2 Pd-Catalyzed Tsuji–Trost Alkylation Reaction7 Other Reactions7.1 Olefination7.2 Heck-Type Reaction7.3 Ullmann-Type Reaction8 Conclusion and Outlook

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Ng, Sze-Sze, Chun-Yu Ho, Kristin D. Schleicher, and Timothy F. Jamison. "Nickel-catalyzed coupling reactions of alkenes." Pure and Applied Chemistry 80, no. 5 (January 1, 2008): 929–39. http://dx.doi.org/10.1351/pac200880050929.

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Several reactions of simple, unactivated alkenes with electrophiles under Ni(0) catalysis are discussed. The coupling of olefins with aldehydes and silyl triflates provides allylic or homoallylic alcohol derivatives, depending on the supporting ligands and, to a lesser extent, the substrates employed. Reaction of alkenes with isocyanates yields N-alkyl acrylamides. In these methods, alkenes act as the functional equivalents of alkenyl- and allylmetal reagents.

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50

Gu, Binjie, Xiaoli Yu, Zhaojun Xu, Feng Pan, and Dawei Wang. "A Single-Step Palladium-Catalysed Synthesis of Naphtho[2,3-b]Benzofuran-6,11-Diones and 2-(Hydroxyphenyl)Naphthalene-1,4-Diones." Journal of Chemical Research 41, no. 10 (October 2017): 564–68. http://dx.doi.org/10.3184/174751917x15045169836235.

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Palladium-catalysed competitive three-component C–H functionalisation reactions and cascade coupling ring-closing reactions of quinones with iodophenols in dihaloalkanes are described. During initial attempts to conduct C–H functionalisation reactions of quinones with iodophenols in dihaloalkanes, surprisingly a three-component C–H functionalisation reaction was discovered. Furthermore, as the reaction of chloroquinones with iodophenols was in progress, another surprising cascade coupling with ring closure was achieved. This provided an efficient single-step synthesis of naphtho[2,3- b]benzofuran-6,11-diones.

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