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Journal articles on the topic 'Cross-coupling reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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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 (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. Poly

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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 (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

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3

Daley, Ryan A., and Joseph J. Topczewski. "Aryl-Decarboxylation Reactions Catalyzed by Palladium: Scope and Mechanism." Synthesis 52, no. 03 (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 pa

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4

Koóš, Peter, Martin Markovič, Pavol Lopatka, and Tibor Gracza. "Recent Applications of Continuous Flow in Homogeneous Palladium Catalysis." Synthesis 52, no. 23 (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 Sy

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5

Akkarasamiyo, Sunisa, Somsak Ruchirawat, Poonsaksi Ploypradith та Joseph S. M. Samec. "Transition-Metal-Catalyzed Suzuki–Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols". Synthesis 52, № 05 (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

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6

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

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7

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

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8

Staubitz, Anne, Melanie Walther, Waldemar Kipke, Sven Schultzke, and Souvik Ghosh. "Modification of Azobenzenes by Cross-Coupling Reactions." Synthesis 53, no. 07 (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 Compone

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9

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

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10

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 (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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11

Morimoto, Koji, Toshifumi Dohi, and Yasuyuki Kita. "Metal-free Oxidative Cross-Coupling Reaction of Aromatic Compounds Containing Heteroatoms." Synlett 28, no. 14 (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 halogenate

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12

Nicholas, Kenneth M., and Chandrasekhar Bandari. "Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides." Synthesis 53, no. 02 (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 amou

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13

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

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14

P., G. More, V. Dalave N., S. Lawand A., and M. Nalawade A. "Palladium catalyzed cross-coupling reactions of organomercurials." Journal of Indian Chemical Society Vol. 86, Jan 2009 (2009): 68–71. https://doi.org/10.5281/zenodo.5807134.

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Department of Chemistry, Solapur University, Solapur-413 255, Maharashtra, India <em>Fax</em> : 91-217-2744770 Ramkrishna Paramhansa College, Osmanabad-413 501, Maharashtra, India <em>Manuscript received 31 January 2008, accepted 9 September 2008</em> The palladium catalyzed cross-coupling reactions of methyl mercury iodide provide a mild, selective and general method for the construction of new C-C bond i.e. for the synthesis of arenes. The reaction proceeds in DMF, in the presence of a nucleophilic catalyst (iodide ion), at room temperature under argon atmosphere. Pd<sup>0</sup> which is gen

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15

Shirakawa, Eiji. "Electron-Catalyzed Cross-Coupling Reactions." Journal of Synthetic Organic Chemistry, Japan 77, no. 5 (2019): 433–41. http://dx.doi.org/10.5059/yukigoseikyokaishi.77.433.

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16

Kashihara, Myuto, and Yoshiaki Nakao. "Cross-Coupling Reactions of Nitroarenes." Accounts of Chemical Research 54, no. 14 (2021): 2928–35. http://dx.doi.org/10.1021/acs.accounts.1c00220.

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17

Dong, Kui, Qiang Liu, and Li-Zhu Wu. "Cross-Coupling Hydrogen Evolution Reactions." Acta Chimica Sinica 78, no. 4 (2020): 299. http://dx.doi.org/10.6023/a19110412.

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18

Pérez Sestelo, José, and Luis A. Sarandeses. "Advances in Cross-Coupling Reactions." Molecules 25, no. 19 (2020): 4500. http://dx.doi.org/10.3390/molecules25194500.

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19

Fürstner, Alois, Andreas Leitner, María Méndez, and Helga Krause. "Iron-Catalyzed Cross-Coupling Reactions." Journal of the American Chemical Society 124, no. 46 (2002): 13856–63. http://dx.doi.org/10.1021/ja027190t.

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20

Suzuki, Akira. "Cross-coupling reactions via organoboranes." Journal of Organometallic Chemistry 653, no. 1-2 (2002): 83–90. http://dx.doi.org/10.1016/s0022-328x(02)01269-x.

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21

Cahiez, Gérard, and Alban Moyeux. "Cobalt-Catalyzed Cross-Coupling Reactions." Chemical Reviews 110, no. 3 (2010): 1435–62. http://dx.doi.org/10.1021/cr9000786.

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22

Gosmini, Corinne, Jeanne-Marie Bégouin, and Aurélien Moncomble. "Cobalt-catalyzed cross-coupling reactions." Chemical Communications, no. 28 (2008): 3221. http://dx.doi.org/10.1039/b805142a.

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23

Beletskaya, Irina P., and Andrei V. Cheprakov. "Copper in cross-coupling reactions." Coordination Chemistry Reviews 248, no. 21-24 (2004): 2337–64. http://dx.doi.org/10.1016/j.ccr.2004.09.014.

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24

Hayashi, Tamio. "ChemInform Abstract: Cross-Coupling Reactions." ChemInform 31, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.200018235.

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25

Stüer, Rainer. "Metal-Catalyzed Cross-Coupling Reactions." Advanced Synthesis & Catalysis 347, no. 1 (2005): 197. http://dx.doi.org/10.1002/adsc.200404362.

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26

Vaaland, Ingrid Caroline, and Magne Olav Sydnes. "Consecutive Palladium Catalyzed Reactions in One-Pot Reactions." Mini-Reviews in Organic Chemistry 17, no. 5 (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 us

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27

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 (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, palla

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28

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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29

Kotha, Sambasivarao, Milind Meshram, and Nageswara Panguluri. "Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions." Synthesis 51, no. 09 (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 Modificati

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30

Li, Gao, and Rongchao Jin. "Catalysis by gold nanoparticles: carbon-carbon coupling reactions." Nanotechnology Reviews 2, no. 5 (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

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31

Wang, Chuan, and Youxiang Jin. "Nickel-Catalyzed Asymmetric Cross-Electrophile Coupling Reactions." Synlett 31, no. 19 (2020): 1843–50. http://dx.doi.org/10.1055/s-0040-1707216.

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The merger of cross-electrophile coupling and asymmetric catalysis provides a novel approach to the preparation of optically active compounds. This method is often endowed with high step economy, mild conditions, and excellent tolerance of functional groups. Recent advances in the research field of nickel-catalyzed asymmetric cross-electrophile coupling reactions are highlighted in this concise Synpacts article.1 Introduction2 Asymmetric Cross-Electrophile Coupling Reactions between Organohalides3 Asymmetric Electrophilic Ring-Opening Reactions4 Asymmetric Electrophilic Difunctionalization of

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32

Tobrman, Tomáš, Tereza Edlová, and Marek Čubiňák. "Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis." Synthesis 53, no. 02 (2020): 255–66. http://dx.doi.org/10.1055/s-0040-1707270.

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AbstractThis short review summarizes the latest advances in the cross-coupling reactions of double and triple electrophilic templates bearing halogen atoms and an activated C–O bond. Reactions involving the formation of a C–C bond as part of di-, tri-, and tetrasubstituted double bond systems are highlighted.1 Introduction2 Cross-Coupling Reactions of Halovinyl Tosylates3 Cross-Coupling Reactions of Halovinyl Triflates4 Cross-Coupling Reactions of Halovinyl Phosphates5 Cross-Coupling Reactions of Halovinyl Esters6 Conclusion

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33

Afsina, C. M. A., Thaipparambil Aneeja, Mohan Neetha, and Gopinathan Anilkumar. "Copper‐Catalyzed Cross‐Dehydrogenative Coupling Reactions." European Journal of Organic Chemistry 2021, no. 12 (2021): 1776–808. http://dx.doi.org/10.1002/ejoc.202001549.

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34

Fernando Gomollón-Bel, special to C&EN. "Enzyme catalyzes biaryl cross-coupling reactions." C&EN Global Enterprise 100, no. 10 (2022): 8. http://dx.doi.org/10.1021/cen-10010-scicon1.

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35

Hoff, Lukas V., Simon D. Schnell, Andrea Tomio, Anthony Linden, and Karl Gademann. "Cross-Coupling Reactions of Monosubstituted Tetrazines." Organic Letters 23, no. 15 (2021): 5689–92. http://dx.doi.org/10.1021/acs.orglett.1c01813.

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36

Matsumoto, Masatoshi, Masashi Harada, Yasuhiro Yamashita, and Shū Kobayashi. "Catalytic imine–imine cross-coupling reactions." Chem. Commun. 50, no. 86 (2014): 13041–44. http://dx.doi.org/10.1039/c4cc06156j.

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37

Pattenden, Gerald, and Davey Stoker. "Stille Cross-Coupling Reactions Using Vinylcyclopropylstannanes." Synlett 2009, no. 11 (2009): 1800–1802. http://dx.doi.org/10.1055/s-0029-1217327.

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38

Mukaiyama, Teruaki, and Masahiro Murakami. "Cross-Coupling Reactions Based on Acetals." Synthesis 1987, no. 12 (1987): 1043–54. http://dx.doi.org/10.1055/s-1987-28167.

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39

Novák, Zoltán, and András Kotschy. "First Cross-Coupling Reactions on Tetrazines." Organic Letters 5, no. 19 (2003): 3495–97. http://dx.doi.org/10.1021/ol035312w.

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40

Nielsen, Mogens, Katrine Qvortrup, Asbjørn Andersson, Jan-Philipp Mayer, and Anne Jepsen. "Cross-Coupling Reactions with Acetylenic Dithiafulvenes." Synlett 2004, no. 15 (2004): 2818–20. http://dx.doi.org/10.1055/s-2004-835641.

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41

Itami, Kenichiro, Koichi Mitsudo, Toshiki Nokami, Toshiyuki Kamei, Tooru Koike, and Jun-ichi Yoshida. "Pyridylsilyl group-driven cross-coupling reactions." Journal of Organometallic Chemistry 653, no. 1-2 (2002): 105–13. http://dx.doi.org/10.1016/s0022-328x(02)01173-7.

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42

Fihri, Aziz, Mohamed Bouhrara, Bijan Nekoueishahraki, Jean-Marie Basset, and Vivek Polshettiwar. "Nanocatalysts for Suzuki cross-coupling reactions." Chemical Society Reviews 40, no. 10 (2011): 5181. http://dx.doi.org/10.1039/c1cs15079k.

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43

Kojima, Akihiko, Shinobu Honzawa, Christopher D. J. Boden, and Masakatsu Shibasaki. "Tandem Suzuki cross-coupling-Heck reactions." Tetrahedron Letters 38, no. 19 (1997): 3455–58. http://dx.doi.org/10.1016/s0040-4039(97)00644-8.

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44

Konev, Mikhail O., and Elizabeth R. Jarvo. "Decarboxylative Alkyl-Alkyl Cross-Coupling Reactions." Angewandte Chemie International Edition 55, no. 38 (2016): 11340–42. http://dx.doi.org/10.1002/anie.201605593.

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45

Hayashi, Tamio. "ChemInform Abstract: Asymmetric Cross-Coupling Reactions." ChemInform 41, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.201035239.

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46

Weinstein, Cory M., Caleb D. Martin, Liu Liu, and Guy Bertrand. "Cross-Coupling Reactions between Stable Carbenes." Angewandte Chemie International Edition 53, no. 25 (2014): 6550–53. http://dx.doi.org/10.1002/anie.201404199.

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47

Minami, Hiroki, Tatsuo Saito, Chao Wang, and Masanobu Uchiyama. "Organoaluminum-Mediated Direct Cross-Coupling Reactions." Angewandte Chemie International Edition 54, no. 15 (2015): 4665–68. http://dx.doi.org/10.1002/anie.201412249.

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48

Weinstein, Cory M., Caleb D. Martin, Liu Liu, and Guy Bertrand. "Cross-Coupling Reactions between Stable Carbenes." Angewandte Chemie 126, no. 25 (2014): 6668–71. http://dx.doi.org/10.1002/ange.201404199.

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49

Minami, Hiroki, Tatsuo Saito, Chao Wang, and Masanobu Uchiyama. "Organoaluminum-Mediated Direct Cross-Coupling Reactions." Angewandte Chemie 127, no. 15 (2015): 4748–51. http://dx.doi.org/10.1002/ange.201412249.

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50

Ogasawara, Masamichi, and Tamio Hayashi. "ChemInform Abstract: Asymmetric Cross-Coupling Reactions." ChemInform 32, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.200129262.

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