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Journal articles on the topic 'C-H Activation/Functionalization'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Muñoz-Molina, José María, Tomás R. Belderrain, and Pedro J. Pérez. "Recent Advances in Copper-Catalyzed Radical C–H Bond Activation Using N–F Reagents." Synthesis 53, no. 01 (2020): 51–64. http://dx.doi.org/10.1055/s-0040-1707234.

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This Short Review is aimed at giving an update in the area of copper-catalyzed C–H functionalization involving nitrogen-centered radicals generated from substrates containing N–F bonds. These processes include intermolecular Csp3–H bond functionalization, remote Csp3–H bond functionalization via intramolecular hydrogen atom transfer (HAT), and Csp2–H bond functionalization, which might be of potential use in industrial applications in the future.1 Introduction2 Intermolecular Csp3–H Functionalization3 Remote Csp3–H Functionalization4 Csp2–H Functionalization5 Conclusion

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2

Senge, Mathias O., and Nitika Grover. "Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules." Synthesis 52, no. 22 (2020): 3295–325. http://dx.doi.org/10.1055/s-0040-1707884.

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The remarkable structural and electronic properties of rigid non-conjugated hydrocarbons afford attractive opportunities to design molecular building blocks for both medicinal and material applications. The bridgehead positions provide the possibility to append diverse functional groups at specific angles and in specific orientations. The current review summarizes the synthetic development in CH functionalization of three rigid scaffolds namely: (a) cubane, (b) bicyclo[1.1.1]pentane (BCP), (c) adamantane.1 Introduction2 Cubane2.1 Cubane Synthesis2.2 Cubane Functionalization3 Bicyclo[1.1.1]pent

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3

Sarpong, Richmond. "C–H Functionalization/activation in organic synthesis." Beilstein Journal of Organic Chemistry 12 (November 3, 2016): 2315–16. http://dx.doi.org/10.3762/bjoc.12.224.

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4

Qiu, Guanyinsheng, and Jie Wu. "Transition metal-catalyzed direct remote C–H functionalization of alkyl groups via C(sp3)–H bond activation." Organic Chemistry Frontiers 2, no. 2 (2015): 169–78. http://dx.doi.org/10.1039/c4qo00207e.

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This review is focused on the recent advances in the transition metal-catalyzed direct remote C–H-functionalization of alkyl groups via C(sp<sup>3</sup>)–H bond activation. In general, carboxamide/ester-chelated β-functionalization reactions are summarized.

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5

Wang, Weixiang, Tianqi Liu, Chang-Hua Ding, and Bin Xu. "C(sp3)–H functionalization with isocyanides." Organic Chemistry Frontiers 8, no. 13 (2021): 3525–42. http://dx.doi.org/10.1039/d1qo00153a.

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This review highlights the state-of-the-art advances in C(sp<sup>3</sup>)–H functionalization involving isocyanides through the synergistic combination of isocyanide insertion and C(sp<sup>3</sup>)–H bond activation.

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6

Shi, Z., S. Yang, B. Li, and X. Wan. "C-H Functionalization via C-H Activation and C-C Bond Formation with Arylsilanes." Synfacts 2007, no. 7 (2007): 0751. http://dx.doi.org/10.1055/s-2007-968643.

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7

Liu, Yichang, Hong Yi, and Aiwen Lei. "Oxidation-Induced C-H Functionalization: A Formal Way for C-H Activation." Chinese Journal of Chemistry 36, no. 8 (2018): 692–97. http://dx.doi.org/10.1002/cjoc.201800106.

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8

ZHAO, Mengdi, and Wenjun LU. "Alkanes Functionalization via C―H Activation." Acta Physico-Chimica Sinica 35, no. 9 (2019): 977–88. http://dx.doi.org/10.3866/pku.whxb201811045.

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9

Roudesly, Fares, Julie Oble, and Giovanni Poli. "Metal-catalyzed C H activation/functionalization: The fundamentals." Journal of Molecular Catalysis A: Chemical 426 (January 2017): 275–96. http://dx.doi.org/10.1016/j.molcata.2016.06.020.

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10

Sinha, Soumya Kumar, Trisha Bhattacharya, and Debabrata Maiti. "Role of hexafluoroisopropanol in C–H activation." Reaction Chemistry & Engineering 4, no. 2 (2019): 244–53. http://dx.doi.org/10.1039/c8re00225h.

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HFIP has developed immense importance in the C–H functionalization methodology. Both the reactivity and selectivity have been vastly improved using HFIP whose H-bonding to the substrate facilitates and accelerates C–H activation. This review summarizes the chronological development of the evolution of HFIP in C–H activation along with important mechanistic details.

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11

Topczewski, Joseph J., and Melanie S. Sanford. "Carbon–hydrogen (C–H) bond activation at PdIV: a Frontier in C–H functionalization catalysis." Chemical Science 6, no. 1 (2015): 70–76. http://dx.doi.org/10.1039/c4sc02591a.

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12

Cheng, Jiang, Xiaopeng Wu, Song Sun та Jin-Tao Yu. "Recent Applications of α-Carbonyl Sulfoxonium Ylides in Rhodium- and Iridium-Catalyzed C–H Functionalizations". Synlett 30, № 01 (2018): 21–29. http://dx.doi.org/10.1055/s-0037-1610263.

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Sulfoxonium ylides are a special type of sulfur ylides that serve as new C1 or C2 synthons recently developed for use in C–H functionalization to access acylmethylated or cyclized compounds through the formation of metal carbene species. Many excellent works have reported the syntheses of various useful skeletons from these versatile synthons. These developments have not previously been completely investigated or reviewed. In this review, we summarize recent advances in the use of α-carbonyl sulfoxonium ylides in C–H functionalizations, including ortho-C–H acylmethylation reactions and ortho-C

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13

Dutta, Uttam, Sudip Maiti, Trisha Bhattacharya, and Debabrata Maiti. "Arene diversification through distal C(sp2)−H functionalization." Science 372, no. 6543 (2021): eabd5992. http://dx.doi.org/10.1126/science.abd5992.

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Transition metal–catalyzed aryl C−H activation is a powerful synthetic tool as it offers step and atom-economical routes to site-selective functionalization. Compared with proximal ortho-C−H activation, distal (meta- and/or para-) C−H activation remains more challenging due to the inaccessibility of these sites in the formation of energetically favorable organometallic pretransition states. Directing the catalyst toward the distal C−H bonds requires judicious template engineering and catalyst design, as well as prudent choice of ligands. This review aims to summarize the recent elegant discove

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14

Uttry, Alexander, and Manuel van Gemmeren. "Direct C(sp3)–H Activation of Carboxylic Acids." Synthesis 52, no. 04 (2019): 479–88. http://dx.doi.org/10.1055/s-0039-1690720.

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Carboxylic acids are important in a variety of research fields and applications. As a result, substantial efforts have been directed towards the C–H functionalization of such compounds. While the use of the carboxylic acid moiety as a native directing group for C(sp2)–H functionalization reactions is well established, as yet there is no general solution for the C(sp3)–H activation of aliphatic carboxylic acids and most endeavors have instead relied on the introduction of stronger directing groups. Recently however, novel ligands, tools, and strategies have emerged, which enable the use of free

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15

Huang, Yao, Wen-Jing Pan, and Zhong-Xia Wang. "Rhodium-catalyzed alkenyl C–H functionalization with amides." Organic Chemistry Frontiers 6, no. 13 (2019): 2284–90. http://dx.doi.org/10.1039/c9qo00489k.

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16

Johnson, S. A. "Nickel complexes for catalytic C–H bond functionalization." Dalton Transactions 44, no. 24 (2015): 10905–13. http://dx.doi.org/10.1039/c5dt00032g.

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17

Arockiam, Percia Beatrice, Christian Bruneau, and Pierre H. Dixneuf. "Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization." Chemical Reviews 112, no. 11 (2012): 5879–918. http://dx.doi.org/10.1021/cr300153j.

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18

Ansel, Annabel Q., and John Montgomery. "Combined Cyanoborylation, C–H Activation Strategy for Styrene Functionalization." Organic Letters 22, no. 21 (2020): 8538–43. http://dx.doi.org/10.1021/acs.orglett.0c03138.

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19

Liron, Frédéric, Julie Oble, Mélanie M. Lorion, and Giovanni Poli. "Direct Allylic Functionalization Through Pd-Catalyzed C-H Activation." European Journal of Organic Chemistry 2014, no. 27 (2014): 5863–83. http://dx.doi.org/10.1002/ejoc.201402049.

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20

Qiu, Guanyinsheng, and Jie Wu. "Correction: Transition metal-catalyzed direct remote C–H functionalization of alkyl groups via C(sp3)–H bond activation." Organic Chemistry Frontiers 2, no. 7 (2015): 859. http://dx.doi.org/10.1039/c5qo90023a.

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Correction for ‘Transition metal-catalyzed direct remote C–H functionalization of alkyl groups via C(sp<sup>3</sup>)–H bond activation’ by Guanyinsheng Qiu, et al., Org. Chem. Front., 2015, 2, 169–178.

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21

Zhang, Bo-Sheng, Hui-Liang Hua, Lu-Yao Gao, et al. "Palladium-catalyzed arene C–H activation/ketone C–H functionalization reaction: route to spirodihydroindenones." Organic Chemistry Frontiers 4, no. 7 (2017): 1376–79. http://dx.doi.org/10.1039/c7qo00164a.

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22

Dodangeh, Mohammad, Ali Ramazani, Malek-Taher Maghsoodlou, Armin Zarei, and Sobhan Rezayati. "Application of Readily Available Metals for C-H Activation." Current Organic Chemistry 24, no. 14 (2020): 1582–609. http://dx.doi.org/10.2174/1385272824999200616114037.

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Catalytic C-H activation is a powerful method for organic synthesis. In recent years, scientists have made great progress by developing transitional metals for catalyzing CH functionalization reaction. In this review, we summarized and highlighted recent progress in C-H activation with copper, cobalt, iron, manganese, and nickel as catalysts.

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23

Ahmed A. El-Sayed, Nahid Y. Khaireldin, and Eman A. El-Hefny. "Review for metal and organocatalysis of heterocyclic C-H functionalization." World Journal of Advanced Research and Reviews 9, no. 1 (2021): 001–30. http://dx.doi.org/10.30574/wjarr.2021.9.1.0071.

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Over the last few decades, signiﬁcant efforts have been put forth towards the C−H bond group functionalization by transition-metalcatalysis and organocatalysis. Several efficient strategies to convert C-H bond to other groups C-C, C-N, C-O bonds have been implemented. The most attractive C-H bond functionalization was the C-H heterocyclic compounds activation that is practical method in organic synthesis. The new C–C, C–N and C–O bond as formed from the C-H bond activation by two diverse ways metal catalysis and/or organocatalysis. The most important is the synthesis of new bioactive heterocyc

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24

Paterson, Andrew J., Sahra St John-Campbell, Mary F. Mahon, Neil J. Press, and Christopher G. Frost. "Catalytic meta-selective C–H functionalization to construct quaternary carbon centres." Chemical Communications 51, no. 64 (2015): 12807–10. http://dx.doi.org/10.1039/c5cc03951g.

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A ruthenium catalyzed meta-selective C–H functionalization of 2-phenylpyridines with tertiary halides is described to establish challenging quaternary carbon centres in a regioselective manner. Preliminary studies suggest the C–H functionalization proceeds through a radical process directed via a remote σ-activation.

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25

Zhang, Fulin, Luoting Xin, Saihu Liao, Xueliang Huang, and Yinghua Yu. "Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents." Synthesis 53, no. 02 (2020): 238–54. http://dx.doi.org/10.1055/s-0040-1707268.

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AbstractTransition-metal-catalyzed direct inert C–H bond functionalization has attracted much attention over the past decades. However, because of the high strain energy of the suspected palladacycle generated via C–H bond palladation, direct functionalization of a C–H bond less than a three-bond distance from a catalyst center is highly challenging. In this short review, we summarize the advances on palladium-catalyzed bridging C–H activation, in which an inert proximal C–H bond palladation is promoted by the elementary step of migratory insertion of an alkene, an alkyne or a metal carbene in

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26

Meng, Guangrong, and Michal Szostak. "Rhodium-Catalyzed C–H Bond Functionalization with Amides by Double C–H/C–N Bond Activation." Organic Letters 18, no. 4 (2016): 796–99. http://dx.doi.org/10.1021/acs.orglett.6b00058.

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27

Lanzi, Matteo, and Gianpiero Cera. "Iron-Catalyzed C–H Functionalizations under Triazole-Assistance." Molecules 25, no. 8 (2020): 1806. http://dx.doi.org/10.3390/molecules25081806.

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3d transition metals-catalyzed C–H bond functionalizations represent nowadays an important tool in organic synthesis, appearing as the most promising alternative to cross-coupling reactions. Among 3d transition metals, iron found widespread application due to its availability and benign nature, and it was established as an efficient catalyst in organic synthesis. In this context, the use of ortho-orientating directing groups (DGs) turned out to be necessary for promoting selective iron-catalyzed C–H functionalization reactions. Very recently, triazoles DGs were demonstrated to be more than an

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28

Maraswami, Manikantha, and Teck-Peng Loh. "Transition-Metal-Catalyzed Alkenyl sp2 C–H Activation: A Short Account." Synthesis 51, no. 05 (2019): 1049–62. http://dx.doi.org/10.1055/s-0037-1611649.

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Alkenes are ubiquitous in Nature and their functionalization continues to attract attention from the scientific community. On the other hand, activation of alkenyl sp2 C–H bonds is challenging due to their chemical properties. In this short account, we elucidate, discuss and describe the utilization of transition-metal catalysts in alkene activation and provide useful strategies to synthesize organic building blocks in an efficient and sustainable manner.1 Introduction2 Breakthrough3 Controlling E/Z, Z/E Selectivity3.1 Esters and Amides as Directing Groups3.2 The Chelation versus Non-Chelation

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29

Matsubara, Tatsuaki. "Regioselective Functionalization of 2-Pyridones through C-H Bond Activation." Journal of Synthetic Organic Chemistry, Japan 73, no. 7 (2015): 753–54. http://dx.doi.org/10.5059/yukigoseikyokaishi.73.753.

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30

Kapdi, Anant R. "ChemInform Abstract: Organometallic Aspects of C-H Bond Activation/Functionalization." ChemInform 44, no. 34 (2013): no. http://dx.doi.org/10.1002/chin.201334223.

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31

Yang, Yang, Masayoshi Nishiura, Haobing Wang, and Zhaomin Hou. "Metal-catalyzed C H activation for polymer synthesis and functionalization." Coordination Chemistry Reviews 376 (December 2018): 506–32. http://dx.doi.org/10.1016/j.ccr.2018.08.017.

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32

Corio, Alessandra, Christine Gravier-Pelletier, and Patricia Busca. "Regioselective Functionalization of Quinolines through C-H Activation: A Comprehensive Review." Molecules 26, no. 18 (2021): 5467. http://dx.doi.org/10.3390/molecules26185467.

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Quinoline is a versatile heterocycle that is part of numerous natural products and countless drugs. During the last decades, this scaffold also became widely used as ligand in organometallic catalysis. Therefore, access to functionalized quinolines is of great importance and continuous efforts have been made to develop efficient and regioselective synthetic methods. In this regard, C-H functionalization through transition metal catalysis, which is nowadays the Graal of organic green chemistry, represents the most attractive strategy. We aim herein at providing a comprehensive review of methods

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33

Zhang, Yuanbin, Tao Wang, Lingyao Wang, et al. "RhIII -Catalyzed Functionalization of closo -Dodecaborates by Selective B−H Activation: Bypassing Competitive C−H Activation." Chemistry - A European Journal 24, no. 59 (2018): 15812–17. http://dx.doi.org/10.1002/chem.201803455.

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34

Xie, Peipei, Wei Guo, Dimei Chen, and Yuanzhi Xia. "Multiple pathways for C–H cleavage in cationic Cp*Rh(iii)-catalyzed C–H activation without carboxylate assistance: a computational study." Catalysis Science & Technology 8, no. 16 (2018): 4005–9. http://dx.doi.org/10.1039/c8cy00870a.

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35

Guillemard, Lucas, and Joanna Wencel-Delord. "When metal-catalyzed C–H functionalization meets visible-light photocatalysis." Beilstein Journal of Organic Chemistry 16 (July 21, 2020): 1754–804. http://dx.doi.org/10.3762/bjoc.16.147.

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While aiming at sustainable organic synthesis, over the last decade particular attention has been focused on two modern fields, C–H bond activation, and visible-light-induced photocatalysis. Couplings through C–H bond activation involve the use of non-prefunctionalized substrates that are directly converted into more complex molecules, without the need of a previous functionalization, thus considerably reduce waste generation and a number of synthetic steps. In parallel, transformations involving photoredox catalysis promote radical reactions in the absence of radical initiators. They are cond

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36

Díaz-Requejo, M. Mar, Tomás R. Belderrain, M. Carmen Nicasio, and Pedro J. Pérez. "The carbene insertion methodology for the catalytic functionalization of unreactive hydrocarbons: No classical C–H activation, but efficient C–H functionalization." Dalton Trans., no. 47 (2006): 5559–66. http://dx.doi.org/10.1039/b610183f.

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37

Renzetti, Andrea, and Kozo Fukumoto. "Synthesis of Phthalides and ,-butenolides by Transition Metal-Catalyzed Activation of C—H Bonds." Molecules 24, no. 4 (2019): 824. http://dx.doi.org/10.3390/molecules24040824.

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Phthalides and ,-butenolides are two related classes of oxygenated heterocycles with a wide range of biological activities. An innovative strategy to prepare these compounds is based on C—H bond functionalization reactions, in which two simple, unfunctionalized molecules are coupled together with cleavage of a C—H bond and formation of a C—X bond (X=C or heteroatom). This paper reviews the methods for the synthesis of phthalides and ,-butenolides by C—H bond functionalization from non-halogenated starting materials. Over 30 methods are reported, mostly developed during the past ten years.

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38

Hu, Fangdong, Ying Xia, Chen Ma, Yan Zhang, and Jianbo Wang. "C–H bond functionalization based on metal carbene migratory insertion." Chemical Communications 51, no. 38 (2015): 7986–95. http://dx.doi.org/10.1039/c5cc00497g.

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39

Borie, Cyril, Lutz Ackermann, and Malek Nechab. "Enantioselective syntheses of indanes: from organocatalysis to C–H functionalization." Chemical Society Reviews 45, no. 5 (2016): 1368–86. http://dx.doi.org/10.1039/c5cs00622h.

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The indanyl core is ubiquitous in a large variety of drugs and natural products. Remarkable recent progress has been accomplished in the step-economical assembly of functionalization of chiral indanes by means of enantioselective catalysis, with major progress being achieved in organocatalysis and C–H activation chemistry.

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40

Reyes, Ronald, and Masaya Sawamura. "An Introductory Overview of C–H Bond Activation/ Functionalization Chemistry with Focus on Catalytic C(sp3)–H Bond Borylation." KIMIKA 32, no. 1 (2021): 70–109. http://dx.doi.org/10.26534/kimika.v32i1.70-109.

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The direct and selective functionalization of C–H bonds provides novel disconnections and innovative strategies to streamline the synthesis of molecules with diverse complexities. However, despite the significant advances in the elaboration of techniques for C–H activation, the utilization of unactivated C(sp3)–H bonds remains challenging. In particular, asymmetric transformation of C(sp3)–H bonds is underdeveloped owing to the lack of catalytic systems that can competently discriminate among ubiquitous C–H bonds in organic molecules. This short review aims to outline the challenges and strate

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41

Kaur, Milanpreet, and Jeffrey F. Van Humbeck. "Recent trends in catalytic sp3 C–H functionalization of heterocycles." Organic & Biomolecular Chemistry 18, no. 4 (2020): 606–17. http://dx.doi.org/10.1039/c9ob01559k.

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42

van Gemmeren, Manuel, та Alexander Uttry. "The Direct Pd-Catalyzed β-C(sp3)–H Activation of Carboxylic Acids". Synlett 29, № 15 (2018): 1937–43. http://dx.doi.org/10.1055/s-0037-1610150.

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The carboxylic acid moiety is one of the most versatile and abundant functional groups. However, despite of tremendous progress in the field of C–H functionalization reactions its use as a directing group for C(sp3)–H activation has remained limited. In this Synpact article we present the challenges associated with the carboxylic acid moiety as a native directing group and report on the newest developments in this field, including our recent study in which we developed a generally applicable protocol for the direct palladium catalyzed β-C(sp3)–H arylation of propionic acid and related α-branch

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43

Cai, Xiao-Hua, Meng-Zhi Yang, and Bing Xie. "Recent Investigations on the Functionalizations of C(sp3)-H Bonds Adjacent to a Heteroatom." Letters in Organic Chemistry 16, no. 10 (2019): 779–801. http://dx.doi.org/10.2174/1570178616666190123131353.

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The selective functionalization of unactivated C(sp3)-H bonds has been regarded as an efficient and atom-economical approach for the formation of carbon-carbon or carbon-heteroatom bonds in modern organic synthesis. Especially, the oxidative activation of C(sp3)–H bonds adjacent to a heteroatom exhibits quite significant features in synthetic chemistry. For example, the direct functionalizations of amines, amides and ethers present important alternative tactics for the synthesis of various novel and useful molecules from simple starting materials. Many remarkable achievements in the area had c

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44

Jia, Xue-Shun, Liang Yin, and Zhao-Kun Li. "Recent Advances in Copper(II)-Mediated or -Catalyzed C–H Functionalization." Synthesis 50, no. 21 (2018): 4165–88. http://dx.doi.org/10.1055/s-0037-1609932.

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This review summarizes recent developments in the field of copper-mediated or -catalyzed C–H functionalization. The substrate scope has been expanded from the C–H activation of aryls to more challenging alkyls. Furthermore, catalytic amounts of copper salt are sufficient to promote the challenging C–H functionalization in some cases, which represents the focus of future research.1 Introduction2 C–C Bond Formation3 C–N Bond Formation4 C–O Bond Formation5 C–Halogen Bond Formation6 C–S Bond Formation7 Conclusions and Outlook

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45

Shan, Chunhui, Lei Zhu, Ling-Bo Qu, Ruopeng Bai, and Yu Lan. "Mechanistic view of Ru-catalyzed C–H bond activation and functionalization: computational advances." Chemical Society Reviews 47, no. 20 (2018): 7552–76. http://dx.doi.org/10.1039/c8cs00036k.

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46

Yuan, Yuan, Shuwei Zhang, Zheng Sun, et al. "Oxidation of the inert sp3 C–H bonds of tetrahydroisoquinolines through C–H activation relay (CHAR): construction of functionalized isoquinolin-1-ones." Chemical Communications 57, no. 27 (2021): 3347–50. http://dx.doi.org/10.1039/d1cc00550b.

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47

Jia, Chengguo, Tsugio Kitamura, and Yuzo Fujiwara. "Catalytic Functionalization of Arenes and Alkanes via C-H Bond Activation." Accounts of Chemical Research 34, no. 10 (2001): 844. http://dx.doi.org/10.1021/ar0101133.

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48

Xue, Xiao-Song, Pengju Ji, Biying Zhou, and Jin-Pei Cheng. "The Essential Role of Bond Energetics in C–H Activation/Functionalization." Chemical Reviews 117, no. 13 (2017): 8622–48. http://dx.doi.org/10.1021/acs.chemrev.6b00664.

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49

Zhang, Shu-Yu, Fu-Min Zhang та Yong-Qiang Tu. "Direct Sp3α-C–H activation and functionalization of alcohol and ether". Chemical Society Reviews 40, № 4 (2011): 1937. http://dx.doi.org/10.1039/c0cs00063a.

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50

Voutchkova, Adelina M., and Robert H. Crabtree. "Iridium-catalyzed benzylic C–H activation and functionalization of alkyl arenes." Journal of Molecular Catalysis A: Chemical 312, no. 1-2 (2009): 1–6. http://dx.doi.org/10.1016/j.molcata.2009.07.019.

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