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Journal articles on the topic 'C-c bond formation reactions'

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Published: 4 June 2021

Last updated: 11 February 2022

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1

Liu, Jialin, Xiaoyu Xiong, Jie Chen, Yuntao Wang, Ranran Zhu, and Jianhui Huang. "Double C–H Activation for the C–C bond Formation Reactions." Current Organic Synthesis 15, no. 7 (October 16, 2018): 882–903. http://dx.doi.org/10.2174/1570179415666180720111422.

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Background: Among the numerous bond-forming patterns, C–C bond formation is one of the most useful tools for building molecules for the chemical industry as well as life sciences. Recently, one of the most challenging topics is the study of the direct coupling reactions via multiple C–H bond cleavage/activation processes. A number of excellent reviews on modern C–H direct functionalization have been reported by Bergman, Bercaw, Yu and others in recent years. Among the large number of available methodologies, Pdcatalyzed reactions and hypervalent iodine reagent mediated reactions represent the most popular metal and non-metal involved transformations. However, the comprehensive summary of the comparison of metal and non-metal mediated transformations is still not available. Objective: The review focuses on comparing these two types of reactions (Pd-catalyzed reactions and hypervalent iodine reagent mediated reactions) based on the ways of forming new C–C bonds, as well as the scope and limitations on the demonstration of their synthetic applications. Conclusion: Comparing the Pd-catalyzed strategies and hypervalent iodine reagent mediated methodologies for the direct C–C bond formation from activation of C-H bonds, we clearly noticed that both strategies are powerful tools for directly obtaining the corresponding pruducts. On one hand, the hypervalent iodine reagents mediated reactions are normally under mild conditions and give the molecular diversity without the presence of transition-metal, while the Pd-catalyzed approaches have a broader scope for the wide synthetic applications. On the other hand, unlike Pd-catalyzed C-C bond formation reactions, the study towards hypervalent iodine reagent mediated methodology mainly focused on the stoichiometric amount of hypervalent iodine reagent, while few catalytic reactions have been reported. Meanwhile, hypervalent iodine strategy has been proved to be more efficient in intramolecular medium-ring construction, while there are less successful examples on C(sp3)–C(sp3) bond formation. In summary, we have demonstrated a number of selected approaches for the formation of a new C–C bond under the utilization of Pd-catalyzed reaction conditions or hyperiodine reagents. The direct activations of sp2 or sp3 hybridized C–H bonds are believed to be important strategies for the future molecular design as well as useful chemical entity synthesis.

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2

Matsuda, Fuyuhiko. "C-C Bond Formation Reactions with SmI2." Journal of Synthetic Organic Chemistry, Japan 59, no. 2 (2001): 92–100. http://dx.doi.org/10.5059/yukigoseikyokaishi.59.92.

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3

Kaur, Mandeep, Opinder Kaur, Rahul Badru, Sandeep Kaushal, and Pritpal Singh. "Ionic Liquid Assisted C-C Bond Formation." Current Organic Chemistry 24, no. 16 (November 9, 2020): 1853–75. http://dx.doi.org/10.2174/1385272824999200801022221.

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With their ability to dissolve inorganic as well as organic materials, ionic liquids have emerged as a versatile solvent system for a diverse range of organic transformations. In the past few decades, the literature has witnessed remarkable advances in a wide range of organic conversions carried out in the presence of various imidazolium, pyridinium, pyrrolidinium, quinolinium and diazobicyclo-octane based ionic liquids. In the reaction, ionic liquids serve as a solvent, catalyst or sometimes both. In certain cases, they are also modified with metal nanoparticles or complexes to form heterogeneous catalysts or are immobilized onto solid support like agar-agar to act as solid-support catalysts. Reactions catalysed by ionic liquids incorporating chiral catalysts possess the advantageous features of being highly enantioselective and reproducible, besides being economical and easy to handle. In this review, an updated insight regarding the role played by ionic liquids in various C-C bond-forming organic reactions, has been summarized.

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4

Mejía, Esteban, and Ahmad A. Almasalma. "Recent Advances on Copper-Catalyzed C–C Bond Formation via C–H Functionalization." Synthesis 52, no. 18 (May 19, 2020): 2613–22. http://dx.doi.org/10.1055/s-0040-1707815.

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Reactions that form C–C bonds are at the heart of many important transformations, both in industry and in academia. From the myriad of catalytic approaches to achieve such transformations, those relying on C–H functionalization are gaining increasing interest due to their inherent sustainable nature. In this short review, we showcase the most recent advances in the field of C–C bond formation via C–H functionalization, but focusing only on those methodologies relying on copper catalysts. This coinage metal has gained increased popularity in recent years, not only because it is cheaper and more abundant than precious metals, but also thanks to its rich and versatile chemistry.1 Introduction2 Cross-Dehydrogenative Coupling under Thermal Conditions2.1 C(sp3)–C(sp3) Bond Formation2.2 C(sp3)–C(sp2) Bond Formation2.3 C(sp2)–C(sp2) Bond Formation2.4 C(sp3)–C(sp) Bond Formation3 Cross-Dehydrogenative Coupling under Photochemical Conditions3.1 C(sp3)–C(sp3) Bond Formation3.2 C(sp3)–C(sp2) and C(sp3)–C(sp) Bond Formation4 Conclusion and Perspective

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5

Puerto Galvis, Carlos, and Vladimir Kouznetsov. "Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids." Synthesis 49, no. 20 (September 21, 2017): 4535–61. http://dx.doi.org/10.1055/s-0036-1589512.

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Among the existing methods for the synthesis of bioactive and/or complex small molecules, organic transformations such as C–C and C–N bond formation have been significantly developed and exploited for the synthesis of diverse synthetic and natural fused aza-polycycles. The abundance and biological and physical activities of 1-phenethyl-tetrahydroisoquinolines, aporphines, homoaporphines, and β-carbolines have inspired many organic chemists to seek sustainable and efficient protocols for their preparation. However, these methodologies involve multiple steps and in most cases the key reaction step is based on the formation of new C–C and/or C–N bonds, and this is usually the critical step that lowers the yields and selectivity. This review is focused on the advances made in recent years regarding the synthesis of these selected natural fused aza-polycycles, overviewing the substrate scope, limitations, regioselectivity, and chemoselectivity, as well as related control strategies of these reactions, concentrating on developments from 2010 to 2016.1 Introduction2 1-Phenethyl-tetrahydroisoquinolines; Dysoxylum Alkaloids3 Aporphines, Homoaporphines, and Semisynthetic Derivatives4 Harmala and Eudistomin Alkaloids and Their Biological Properties5 Metal-Catalyzed C–C Bond Formation6 Pd-Catalyzed C–C and C–N Bond Formation7 Metal-Catalyzed C–N Bond Formation8 [4+2] Cycloaddition in the Synthesis Of Aporphines9 Tandem C–N/C–C Bond Formation: The Pictet–Spengler Reaction10 Miscellaneous Methods11 Conclusions

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6

Beletskaya, Irina P. "Palladium catalyzed C-C and C-heteroatom bond formation reactions." Pure and Applied Chemistry 69, no. 3 (January 1, 1997): 471–76. http://dx.doi.org/10.1351/pac199769030471.

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7

Ma, Dongge, Anan Liu, Shuhong Li, Chichong Lu, and Chuncheng Chen. "TiO2 photocatalysis for C–C bond formation." Catalysis Science & Technology 8, no. 8 (2018): 2030–45. http://dx.doi.org/10.1039/c7cy01458a.

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8

Saavedra, Beatriz, Alessandro Meli, Carla Rizzo, Diego J. Ramón, and Francesca D'Anna. "Natural eutectogels: sustainable catalytic systems for C–C bond formation reactions." Green Chemistry 23, no. 17 (2021): 6555–65. http://dx.doi.org/10.1039/d1gc01647d.

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9

Rao, Bin, and Rei Kinjo. "Boron-Based Catalysts for C−C Bond-Formation Reactions." Chemistry - An Asian Journal 13, no. 10 (May 2, 2018): 1279–92. http://dx.doi.org/10.1002/asia.201701796.

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10

Subrahmanyam, Ayyagari V., Sankaran Thayumanavan, and George W. Huber. "CC Bond Formation Reactions for Biomass-Derived Molecules." ChemSusChem 3, no. 10 (August 24, 2010): 1158–61. http://dx.doi.org/10.1002/cssc.201000136.

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11

Matsuda, Fuyuhiko. "ChemInform Abstract: C-C Bond Formation Reactions with SmI2." ChemInform 32, no. 31 (May 25, 2010): no. http://dx.doi.org/10.1002/chin.200131267.

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12

Wang, Yi, Anan Liu, Dongge Ma, Shuhong Li, Chichong Lu, Tao Li, and Chuncheng Chen. "TiO2 Photocatalyzed C–H Bond Transformation for C–C Coupling Reactions." Catalysts 8, no. 9 (August 27, 2018): 355. http://dx.doi.org/10.3390/catal8090355.

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Fulfilling the direct inert C–H bond functionalization of raw materials that are earth-abundant and commercially available for the synthesis of diverse targeted organic compounds is very desirable and its implementation would mean a great reduction of the synthetic steps required for substrate prefunctionalization such as halogenation, borylation, and metalation. Successful C–H bond functionalization mainly resorts to homogeneous transition-metal catalysis, albeit sometimes suffering from poor catalyst reusability, nontrivial separation, and severe biotoxicity. TiO2 photocatalysis displays multifaceted advantages, such as strong oxidizing ability, high chemical stability and photostability, excellent reusability, and low biotoxicity. The chemical reactions started and delivered by TiO2 photocatalysts are well known to be widely used in photocatalytic water-splitting, organic pollutant degradation, and dye-sensitized solar cells. Recently, TiO2 photocatalysis has been demonstrated to possess the unanticipated ability to trigger the transformation of inert C–H bonds for C–C, C–N, C–O, and C–X bond formation under ultraviolet light, sunlight, and even visible-light irradiation at room temperature. A few important organic products, traditionally synthesized in harsh reaction conditions and with specially functionalized group substrates, are continuously reported to be realized by TiO2 photocatalysis with simple starting materials under very mild conditions. This prominent advantage—the capability of utilizing cheap and readily available compounds for highly selective synthesis without prefunctionalized reactants such as organic halides, boronates, silanes, etc.—is attributed to the overwhelmingly powerful photo-induced hole reactivity of TiO2 photocatalysis, which does not require an elevated reaction temperature as in conventional transition-metal catalysis. Such a reaction mechanism, under typically mild conditions, is apparently different from traditional transition-metal catalysis and beyond our insights into the driving forces that transform the C–H bond for C–C bond coupling reactions. This review gives a summary of the recent progress of TiO2 photocatalytic C–H bond activation for C–C coupling reactions and discusses some model examples, especially under visible-light irradiation.

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13

Xu, Da-Zhen, Ren-Ming Hu, and Yi-Huan Lai. "Iron-Catalyzed Aerobic Oxidative Cross-Dehydrogenative C(sp3)–H/X–H (X = C, N, S) Coupling Reactions." Synlett 31, no. 18 (July 21, 2020): 1753–59. http://dx.doi.org/10.1055/s-0040-1707195.

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The direct functionalization of C(sp3)–H bonds is an attractive research topic in organic synthetic chemistry. The cross-dehydrogenative coupling (CDC) reaction provides a simple and powerful tool for the construction of C–C and C–heteroatom bonds. Recently, some progress has been made in the iron-catalyzed aerobic oxidative CDC reactions. Here, we present recent developments in the direct functionalization of C(sp3)–H bonds catalyzed by simple iron salts with molecular oxygen as the terminal oxidant.1 Introduction2 C(sp3)–C Bond Formation3 C(sp3)–N Bond Formation4 C(sp3)–S(Se) Bond Formation5 Conclusion and Outlook

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14

Eftaiha, Ala'a F., Abdussalam K. Qaroush, Ibrahim K. Okashah, Fatima Alsoubani, Jonas Futter, Carsten Troll, Bernhard Rieger, and Khaleel I. Assaf. "CO2 activation through C–N, C–O and C–C bond formation." Physical Chemistry Chemical Physics 22, no. 3 (2020): 1306–12. http://dx.doi.org/10.1039/c9cp05961j.

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15

Wu, Xiao-Feng, and Helfried Neumann. "Zinc-Catalyzed Organic Synthesis: CC, CN, CO Bond Formation Reactions." Advanced Synthesis & Catalysis 354, no. 17 (November 12, 2012): 3141–60. http://dx.doi.org/10.1002/adsc.201200547.

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16

Liu, Zhenxing, and Jianbo Wang. "Cross-Coupling Reactions Involving Metal Carbene: From C═C/C–C Bond Formation to C–H Bond Functionalization." Journal of Organic Chemistry 78, no. 20 (September 19, 2013): 10024–30. http://dx.doi.org/10.1021/jo401850q.

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17

Shanshal, Muthana Abduljabbar, and Qhatan Adnan Yusuf. "C-C and C-H bond cleavage reactions in acenaphthylene aromatic molecule, an ab-initio density functional theory study." European Journal of Chemistry 10, no. 4 (December 31, 2019): 403–8. http://dx.doi.org/10.5155/eurjchem.10.4.403-408.1889.

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The ab-initio DFT method (B3LYP) is applied to the study of the C-C and C-H bond cleavage reactions in acenaphthylene molecule. It is found that the C-C bond cleavage proceeds via a singlet aromatic transition state, compelled through a disrotatoric ring opening reaction. A sigmatropic H atom shift follows the transition state in some of these reactions, where the formation of a methylene -CH2,acetylenyl-, allenyl- or butadienyl moiety in the final product is possible. The calculated activation and reaction energies for the C-C ring opening are 164-236 and 52-193 kcal/mol, respectively. The calculated cleavage reaction energies for the C-H bonds are 117-122 kcal/mol and the activation energies are 147-164 kcal/mol.

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18

Henry, Martyn, Mohamed Mostafa, and Andrew Sutherland. "Recent Advances in Transition-Metal-Catalyzed, Directed Aryl C–H/N–H Cross-Coupling Reactions." Synthesis 49, no. 20 (August 28, 2017): 4586–98. http://dx.doi.org/10.1055/s-0036-1588536.

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Amination and amidation of aryl compounds using a transition-metal-catalyzed cross-coupling reaction typically involves prefunctionalization or preoxidation of either partner. In recent years, a new class of transition-metal-catalyzed cross-dehydrogenative coupling reaction has been developed for the direct formation of aryl C–N bonds. This short review highlights the substantial progress made for ortho-C–N bond formation via transition-metal-catalyzed chelation-directed aryl C–H activation and gives an overview of the challenges that remain for directed meta- and para-selective reactions.1 Introduction2 Intramolecular C–N Cross-Dehydrogenative Coupling2.1 Nitrogen Functionality as Both Coupling Partner and Directing Group2.2 Chelating-Group-Directed Intramolecular C–N Bond Formation3 Intermolecular C–N Cross-Dehydrogenative Coupling3.1 ortho-C–N Bond Formation3.1.1 Copper-Catalyzed Reactions3.1.2 Other Transition-Metal-Catalyzed Reactions3.2 meta- and para-C–N Bond Formation4 C–N Cross-Dehydrogenative Coupling of Acidic C–H Bonds5 Conclusions

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19

Ding, Yan, He Huang, and Yi Hu. "New Progress on Lipases Catalyzed C—C Bond Formation Reactions." Chinese Journal of Organic Chemistry 33, no. 5 (2013): 905. http://dx.doi.org/10.6023/cjoc2012010050.

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20

Yasukawa, Tomohiro, Hiroyuki Miyamura, and Shū Kobayashi. "Chiral metal nanoparticle-catalyzed asymmetric C–C bond formation reactions." Chem. Soc. Rev. 43, no. 5 (2014): 1450–61. http://dx.doi.org/10.1039/c3cs60298b.

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21

BELETSKAYA, I. P. "ChemInform Abstract: Palladium Catalyzed C-C and C-Heteroatom Bond Formation Reactions." ChemInform 28, no. 28 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199728255.

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22

Saporito, Dafne, Sergio A. Rodriguez, and Maria T. Baumgartner. "Visible Light-Promoted C–C Bond Formation from Hydroxyaryls in Water." Australian Journal of Chemistry 72, no. 12 (2019): 978. http://dx.doi.org/10.1071/ch19378.

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An eco-friendly and direct arylation of hydroxyaryls in water using photoinduced reactions with different substrates (1-bromo-2-naphthol, 1-iodo-2-naphthol, N-(2-iodophenyl)acetamide, 5-bromouracil, 2-iodo-N-methylbenzamide, and 2-iodobenzamide) was studied. For example, π-expanded coumarins, compounds with potential optical applications, were synthesized in very high yield, without the use of toxic reagents, in a one-pot reaction. In addition, we demonstrate that the irradiation source (halogen lamp) can be efficiently replaced by an LED without altering the reaction yield.

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23

Chen, Tieqiao, and Li-Biao Han. "Nickel-Catalyzed CO/CH Cross-Coupling Reactions for CC Bond Formation." Angewandte Chemie International Edition 54, no. 30 (June 12, 2015): 8600–8602. http://dx.doi.org/10.1002/anie.201503204.

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24

Xu, Yulong, Xiaonan Shi, and Lipeng Wu. "tBuOK-triggered bond formation reactions." RSC Advances 9, no. 41 (2019): 24025–29. http://dx.doi.org/10.1039/c9ra04242c.

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25

Zhao, Shibin, Tobias Gensch, Benjamin Murray, Zachary L. Niemeyer, Matthew S. Sigman, and Mark R. Biscoe. "Enantiodivergent Pd-catalyzed C–C bond formation enabled through ligand parameterization." Science 362, no. 6415 (September 20, 2018): 670–74. http://dx.doi.org/10.1126/science.aat2299.

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Despite the enormous potential for the use of stereospecific cross-coupling reactions to rationally manipulate the three-dimensional structure of organic molecules, the factors that control the transfer of stereochemistry in these reactions remain poorly understood. Here we report a mechanistic and synthetic investigation into the use of enantioenriched alkylboron nucleophiles in stereospecific Pd-catalyzed Suzuki cross-coupling reactions. By developing a suite of molecular descriptors of phosphine ligands, we could apply predictive statistical models to select or design distinct ligands that respectively promoted stereoinvertive and stereoretentive cross-coupling reactions. Stereodefined branched structures were thereby accessed through the predictable manipulation of absolute stereochemistry, and a general model for the mechanism of alkylboron transmetallation was proposed.

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26

Anand, Devireddy, Yuwei He, Linyong Li, and Lei Zhou. "A photocatalytic sp3 C–S, C–Se and C–B bond formation through C–C bond cleavage of cycloketone oxime esters." Organic & Biomolecular Chemistry 17, no. 3 (2019): 533–40. http://dx.doi.org/10.1039/c8ob02987c.

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The photocatalytic sulfuration, selenylation and borylation of cycloketone oxime esters through iminyl radical-triggered C–C bond cleavage were described. The reactions provide a unified approach to alkyl sulfur, selenium and boron compounds tethered to a synthetically useful nitrile group.

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27

Bhunia, Subhajit, Govind Goroba Pawar, S. Vijay Kumar, Yongwen Jiang, and Dawei Ma. "Selected Copper-Based Reactions for C−N, C−O, C−S, and C−C Bond Formation." Angewandte Chemie International Edition 56, no. 51 (November 15, 2017): 16136–79. http://dx.doi.org/10.1002/anie.201701690.

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28

Takale, Balaram S., Ruchita R. Thakore, Elham Etemadi-Davan, and Bruce H. Lipshutz. "Recent advances in Cu-catalyzed C(sp3)–Si and C(sp3)–B bond formation." Beilstein Journal of Organic Chemistry 16 (April 15, 2020): 691–737. http://dx.doi.org/10.3762/bjoc.16.67.

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Numerous reactions generating C–Si and C–B bonds are in focus owing to the importance of incorporating silicon or boron into new or existing drugs, in addition to their use as building blocks in cross-coupling reactions en route to various targets of both natural and unnatural origins. In this review, recent protocols relying on copper-catalyzed sp3 carbon–silicon and carbon–boron bond-forming reactions are discussed.

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29

Liu, Zhenxing, and Jianbo Wang. "ChemInform Abstract: Cross-Coupling Reactions Involving Metal Carbene: From C=C/C-C Bond Formation to C-H Bond Functionalization." ChemInform 45, no. 9 (February 14, 2014): no. http://dx.doi.org/10.1002/chin.201409241.

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30

Zagidullin, Almaz A., Il’yas F. Sakhapov, Vasili A. Miluykov, and Dmitry G. Yakhvarov. "Nickel Complexes in C‒P Bond Formation." Molecules 26, no. 17 (August 31, 2021): 5283. http://dx.doi.org/10.3390/molecules26175283.

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This review is a comprehensive account of reactions with the participation of nickel complexes that result in the formation of carbon–phosphorus (C‒P) bonds. The catalytic and non-catalytic reactions with the participation of nickel complexes as the catalysts and the reagents are described. The various classes of starting compounds and the products formed are discussed individually. The several putative mechanisms of the nickel catalysed reactions are also included, thereby providing insights into both the synthetic and the mechanistic aspects of this phosphorus chemistry.

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31

Ma, Dongge, Yi Wang, Anan Liu, Shuhong Li, Chichong Lu, and Chuncheng Chen. "Covalent Organic Frameworks: Promising Materials as Heterogeneous Catalysts for C-C Bond Formations." Catalysts 8, no. 9 (September 19, 2018): 404. http://dx.doi.org/10.3390/catal8090404.

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Covalent organic frameworks (COFs) are defined as highly porous and crystalline polymers, constructed and connected via covalent bonds, extending in two- or three-dimension. Compared with other porous materials such as zeolite and active carbon, the versatile and alternative constituent elements, chemical bonding types and characteristics of ordered skeleton and pore, enable the rising large family of COFs more available to diverse applications including gas separation and storage, optoelectronics, proton conduction, energy storage and in particular, catalysis. As the representative candidate of next-generation catalysis materials, because of their large surface area, accessible and size-tunable open nano-pores, COFs materials are suitable for incorporating external useful active ingredients such as ligands, complexes, even metal nanoparticles deposition and substrate diffusion. These advantages make it capable to catalyze a variety of useful organic reactions such as important C-C bond formations. By appropriate pore-engineering in COFs materials, even enantioselective asymmetric C-C bond formations could be realized with excellent yield and ee value in much shorter reaction time compared with their monomer and oligomer analogues. This review will mainly introduce and discuss the paragon examples of COFs materials for application in C-C bond formation reactions for the organic synthetic purpose.

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32

Rodríguez, Nuria, and Lukas J. Goossen. "Decarboxylative coupling reactions: a modern strategy for C–C-bond formation." Chemical Society Reviews 40, no. 10 (2011): 5030. http://dx.doi.org/10.1039/c1cs15093f.

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33

Terao, Jun, and Nobuaki Kambe. "Transition Metal-Catalyzed C–C Bond Formation Reactions Using Alkyl Halides." Bulletin of the Chemical Society of Japan 79, no. 5 (May 2006): 663–72. http://dx.doi.org/10.1246/bcsj.79.663.

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34

O'Leary, Shane R., Harry Adams, Neil A. Bailey, and Peter M. Maitlis. "C–C Bond formation in organoruthenium complexes by Friedel–Crafts reactions." J. Chem. Soc., Chem. Commun., no. 19 (1995): 2019–20. http://dx.doi.org/10.1039/c39950002019.

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35

Yoshikai, Naohiko. "Recent Advances in Enantioselective C–C Bond Formation via Organocobalt Species." Synthesis 51, no. 01 (December 3, 2018): 135–45. http://dx.doi.org/10.1055/s-0037-1610397.

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This Short Review describes recent developments in cobalt-catalyzed enantioselective C–C bond-forming reactions. The article focuses on reactions that most likely involve chiral organocobalt species as crucial catalytic intermediates and their mechanistic aspects.1 Introduction2 Hydrovinylation3 C–H Functionalization4 Cycloaddition and Cyclization5 Addition of Carbon Nucleophiles6 Cross-Coupling7 Conclusion

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36

Terao, Jun, Hirohisa Todo, Hiroyasu Watabe, Aki Ikumi, Yoshiaki Shinohara, and Nobuaki Kambe. "Carbon-carbon bond-forming reactions using alkyl fluorides." Pure and Applied Chemistry 80, no. 5 (January 1, 2008): 941–51. http://dx.doi.org/10.1351/pac200880050941.

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This account reviews C-C bond formation reactions using alkyl fluorides mostly focusing on the transition-metal-catalyzed reactions. These reactions proceed efficiently under mild conditions by the combined use of Grignard reagents and transition-metal catalysts, such as Ni, Cu, and Zr. It is proposed that ate complex intermediates formed by the reaction of these transition metals with Grignard reagents play important roles as the active catalytic species. Organoaluminun reagents react directly with alkyl fluorides in nonpolar solvents at room temperature to form C-C bonds. These studies demonstrate the practical usefulness of alkyl fluorides in C-C bond formation reactions and provide a promising method for the construction of carbon frameworks employing alkyl fluorides. The scope and limitations, as well as reaction pathways, are discussed.

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37

Wu, Xiao-Feng, and Helfried Neumann. "ChemInform Abstract: Zinc-Catalyzed Organic Synthesis: C-C, C-N, C-O Bond Formation Reactions." ChemInform 44, no. 18 (April 11, 2013): no. http://dx.doi.org/10.1002/chin.201318213.

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38

Kühbeck, Dennis, Basab Bijayi Dhar, Eva-Maria Schön, Carlos Cativiela, Vicente Gotor-Fernández, and David Díaz Díaz. "C–C Bond formation catalyzed by natural gelatin and collagen proteins." Beilstein Journal of Organic Chemistry 9 (June 7, 2013): 1111–18. http://dx.doi.org/10.3762/bjoc.9.123.

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The activity of gelatin and collagen proteins towards C–C bond formation via Henry (nitroaldol) reaction between aldehydes and nitroalkanes is demonstrated for the first time. Among other variables, protein source, physical state and chemical modification influence product yield and kinetics, affording the nitroaldol products in both aqueous and organic media under mild conditions. Significantly, the scale-up of the process between 4-nitrobenzaldehyde and nitromethane is successfully achieved at 1 g scale and in good yield. A comparative kinetic study with other biocatalysts shows an increase of the first-order rate constant in the order chitosan < gelatin < bovine serum albumin (BSA) < collagen. The results of this study indicate that simple edible gelatin can promote C–C bond forming reactions under physiological conditions, which may have important implications from a metabolic perspective.

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39

Choudhuri, Khokan, Milan Pramanik, and Prasenjit Mal. "Noncovalent Interactions in C–S Bond Formation Reactions." Journal of Organic Chemistry 85, no. 19 (August 25, 2020): 11997–2011. http://dx.doi.org/10.1021/acs.joc.0c01534.

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40

Cai, Bao-Gui, Jun Xuan, and Wen-Jing Xiao. "Visible light-mediated C P bond formation reactions." Science Bulletin 64, no. 5 (March 2019): 337–50. http://dx.doi.org/10.1016/j.scib.2019.02.002.

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41

Gao, Jian, Jie Feng, and Ding Du. "Shining Light on C−S Bonds: Recent Advances in C−C Bond Formation Reactions via C−S Bond Cleavage under Photoredox Catalysis." Chemistry – An Asian Journal 15, no. 22 (October 14, 2020): 3637–59. http://dx.doi.org/10.1002/asia.202000905.

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42

Raza, A. L., and T. Braun. "Consecutive C–F bond activation and C–F bond formation of heteroaromatics at rhodium: the peculiar role of FSi(OEt)3." Chemical Science 6, no. 7 (2015): 4255–60. http://dx.doi.org/10.1039/c5sc00877h.

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C–F activation reactions for a silyl complex gave fluorosilane and Rh pyridyl complexes. In consecutive reactions, the fluorosilane can act as a fluoride source and a regeneration of the C–F bond occurs by Si–F bond cleavage. This sets back the C–F bond cleavage reaction with consequences for the overall chemoselectivity of the activation reactions.

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43

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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Zhang, Ji-Shu, Tieqiao Chen, Jia Yang, and Li-Biao Han. "Nickel-catalysed P–C bond formation via P–H/C–CN cross coupling reactions." Chemical Communications 51, no. 35 (2015): 7540–42. http://dx.doi.org/10.1039/c5cc01182e.

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Nickel-catalysed P–H/C–CN cross coupling reactions take place efficiently under mild reaction conditions affording the corresponding sp²C–P bonds. This transformation provides a convenient method for the preparation of both arylphosphines and arylphosphine oxides from the readily available P–H compounds and arylnitriles.

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45

Khusnutdinova, Julia R., and Liviu M. Mirica. "ChemInform Abstract: Organometallic PdIII Complexes in C-C and C-Heteroatom Bond Formation Reactions." ChemInform 45, no. 24 (June 2, 2014): no. http://dx.doi.org/10.1002/chin.201424251.

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46

Helgeland, Ida, and Magne Sydnes. "A Concise Synthesis of Isocryptolepine by C–C Cross-Coupling Followed by a Tandem C–H Activation and C–N Bond Formation." SynOpen 01, no. 01 (March 2017): 0041–44. http://dx.doi.org/10.1055/s-0036-1590807.

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Isocryptolepine (1), a potent antimalarial natural product, was prepared in three steps from 3-bromoquinoline and 2-aminophenylboronic acid hydrochloride. The key transformations were a Suzuki–Miyaura cross-coupling reaction followed by a palladium-initiated intramolecular C–H activation/C–N bond formation between an unprotected amine and an aromatic C–H group. The two key reactions can also be performed in one pot.

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47

Chen, Tieqiao, and Li-Biao Han. "ChemInform Abstract: Nickel-Catalyzed C-O/C-H Cross-Coupling Reactions for C-C Bond Formation." ChemInform 46, no. 36 (August 20, 2015): no. http://dx.doi.org/10.1002/chin.201536283.

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48

Yang, Qiaoyu, Xiaoxian Guo, Yuwan Liu, and Huifeng Jiang. "Biocatalytic C-C Bond Formation for One Carbon Resource Utilization." International Journal of Molecular Sciences 22, no. 4 (February 14, 2021): 1890. http://dx.doi.org/10.3390/ijms22041890.

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The carbon-carbon bond formation has always been one of the most important reactions in C1 resource utilization. Compared to traditional organic synthesis methods, biocatalytic C-C bond formation offers a green and potent alternative for C1 transformation. In recent years, with the development of synthetic biology, more and more carboxylases and C-C ligases have been mined and designed for the C1 transformation in vitro and C1 assimilation in vivo. This article presents an overview of C-C bond formation in biocatalytic C1 resource utilization is first provided. Sets of newly mined and designed carboxylases and ligases capable of catalyzing C-C bond formation for the transformation of CO2, formaldehyde, CO, and formate are then reviewed, and their catalytic mechanisms are discussed. Finally, the current advances and the future perspectives for the development of catalysts for C1 resource utilization are provided.

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Guo, Wei, Mingming Zhao, Wen Tan, Lvyin Zheng, Kailiang Tao, and Xiaolin Fan. "Developments towards synthesis of N-heterocycles from amidines via C–N/C–C bond formation." Organic Chemistry Frontiers 6, no. 13 (2019): 2120–41. http://dx.doi.org/10.1039/c9qo00283a.

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50

De Mesmaeker, Alain, Pascale Hoffmann, and Beat Ernst. "Stereoselective CC bond formation in carbohydrates by radical cyclization reactions-I." Tetrahedron Letters 29, no. 50 (January 1988): 6585–86. http://dx.doi.org/10.1016/s0040-4039(00)82403-x.

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