Journal articles: 'Activation de la liaison C(sp2)-H'

1

Wencel-Delord, Joanna, and Françoise Colobert. "Asymmetric C(sp2)H Activation." Chemistry - A European Journal 19, no. 42 (September 17, 2013): 14010–17. http://dx.doi.org/10.1002/chem.201302576.

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Wencel-Delord, Joanna, and Francoise Colobert. "ChemInform Abstract: Asymmetric C(sp2)-H Activation." ChemInform 45, no. 2 (December 19, 2013): no. http://dx.doi.org/10.1002/chin.201402241.

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3

Bakthadoss, Manickam, Tadiparthi Thirupathi Reddy, Vishal Agarwal, and Duddu S. Sharada. "Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination." Chemical Communications 58, no. 9 (2022): 1406–9. http://dx.doi.org/10.1039/d1cc06097j.

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An orthogonal cross-coupling between aromatic C(sp2) and aliphatic olefinic C(sp2) carbons of two same molecules via dual C–H activation and ortho C–H olefination with various alkenes via distal ester directing group has been developed for the first time.

4

Dutta, Uttam, Sudip Maiti, Trisha Bhattacharya, and Debabrata Maiti. "Arene diversification through distal C(sp2)−H functionalization." Science 372, no. 6543 (May 13, 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 discoveries exploiting directing group assistance, transient mediators or traceless directors, noncovalent interactions, and catalyst and/or ligand selection to control distal C−H activation.

5

Zhang, Yanghui, Bo Zhou, and Ailan Lu. "Pd-Catalyzed C–H Silylation Reactions with Disilanes." Synlett 30, no. 06 (December 18, 2018): 685–93. http://dx.doi.org/10.1055/s-0037-1610339.

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Pd-catalyzed C–H silylation reactions remain underdeveloped. General strategies usually rely on the use of complex bidentate directing groups. C,C-Palladacycles exhibit extremely high reactivity towards hexamethyldisilane and can be disilylated very efficiently. The C,C-palladacycles are prepared through halide-directed C–H activation. This account introduces Pd-catalyzed C–H silylation reactions with disilanes as the silyl source, and is focused on studies on the silylation of C,C-palladacycles.1 Introduction and Background2 Allylic C–H Silylation Reaction3 Coordinating-Ligand-Directed C–H Silylation Reaction4 Disilylation of C(sp2),C(sp2)-Palladacycles That are Generated by C(sp2)–H activation5 Disilylation of C(sp2),C(sp3)-Palladacycles That are Generated by C(sp3)–H Activation6 Disilylation of C,C-Palladacycles That are Generated through Domino Processes7 Summary and Outlook

6

Britton, Luke, Jamie H. Docherty, Andrew P. Dominey, and Stephen P. Thomas. "Iron-Catalysed C(sp2)-H Borylation Enabled by Carboxylate Activation." Molecules 25, no. 4 (February 18, 2020): 905. http://dx.doi.org/10.3390/molecules25040905.

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Arene C(sp2)-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. Applying an in situ catalyst activation method using air-stable and easily handed reagents, the iron-catalysed C(sp2)-H borylation reactions of furans and thiophenes under blue light irradiation have been developed. Key reaction intermediates have been prepared and characterised, and suggest two mechanistic pathways are in action involving both C-H metallation and the formation of an iron boryl species.

7

Geng, Cuihuan, Sujuan Zhang, Chonggang Duan, Tongxiang Lu, Rongxiu Zhu, and Chengbu Liu. "Theoretical investigation of gold-catalyzed oxidative Csp3–Csp2 bond formation via aromatic C–H activation." RSC Advances 5, no. 97 (2015): 80048–56. http://dx.doi.org/10.1039/c5ra16359e.

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The mechanisms of Selectfluor-mediated homogeneous Au-catalyzed intramolecular C_sp3–C_sp2 cross-coupling reaction involving direct aryl C_sp2–H functionalization has been investigated theoretically.

8

Song, Liangliang, Guilong Tian, Johan Van der Eycken, and Erik V. Van der Eycken. "Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp2)–H activation and C(sp3)–H amination." Beilstein Journal of Organic Chemistry 15 (February 27, 2019): 571–76. http://dx.doi.org/10.3762/bjoc.15.52.

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A rhodium(III)-catalyzed intramolecular oxidative annulation of O-substituted N-hydroxyacrylamides for the construction of indolizinones via sequential C(sp2)–H activation and C(sp3)–H amination has been developed. This approach shows excellent functional-group tolerance. The synthesized scaffold forms the core of many natural products with pharmacological relevance.

9

Moghimi, Setareh, Mohammad Mahdavi, Abbas Shafiee, and Alireza Foroumadi. "Transition-Metal-Catalyzed Acyloxylation: Activation of C(sp2)-H and C(sp3)-H Bonds." European Journal of Organic Chemistry 2016, no. 20 (June 19, 2016): 3282–99. http://dx.doi.org/10.1002/ejoc.201600138.

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Dhara, Shubhendu, Raju Singha, Atiur Ahmed, Haridas Mandal, Munmun Ghosh, Yasin Nuree, and Jayanta K. Ray. "Synthesis of α, β and γ-carbolines via Pd-mediated Csp2-H/N–H activation." RSC Adv. 4, no. 85 (2014): 45163–67. http://dx.doi.org/10.1039/c4ra08457h.

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An efficient method for the synthesis of halo-carbolines has been developed via Pd-catalysed formation of C–N bonds through C_sp2-H/N–H activation of 4-methyl-N-[2-(pyridine-3-yl)phenyl] benzenesulfonamide derivatives.

11

Shin, Seohyun, Dongjin Kang, Woo Hyung Jeon, and Phil Ho Lee. "Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp2)–H activation/C–O formation." Beilstein Journal of Organic Chemistry 10 (May 23, 2014): 1220–27. http://dx.doi.org/10.3762/bjoc.10.120.

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We report an efficient Pd-catalyzed C(sp2)–H activation/C–O bond formation for the synthesis of ethoxy dibenzooxaphosphorin oxides from 2-(aryl)arylphosphonic acid monoethyl esters under aerobic conditions.

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Zhang, Hongyu, and Shangdong Yang. "Palladium-catalyzed R2(O)P-directed C(sp2)-H activation." Science China Chemistry 58, no. 8 (April 15, 2015): 1280–85. http://dx.doi.org/10.1007/s11426-015-5382-1.

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13

Sahoo, Sumeet Ranjan, Subhabrata Dutta, Shaeel A. Al-Thabaiti, Mohamed Mokhtar, and Debabrata Maiti. "Transition metal catalyzed C–H bond activation by exo-metallacycle intermediates." Chemical Communications 57, no. 90 (2021): 11885–903. http://dx.doi.org/10.1039/d1cc05042g.

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14

Sun, Qiao, and Naohiko Yoshikai. "Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer." Organic Chemistry Frontiers 5, no. 4 (2018): 582–85. http://dx.doi.org/10.1039/c7qo00906b.

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15

Li, Guang-Hui, Dao-Qing Dong, Xian-Yong Yu, and Zu-Li Wang. "Direct synthesis of 8-acylated quinoline N-oxidesviapalladium-catalyzed selective C–H activation and C(sp2)–C(sp2) cleavage." New Journal of Chemistry 43, no. 4 (2019): 1667–70. http://dx.doi.org/10.1039/c8nj05374j.

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An efficient method for the synthesis of 8-acylated quinoline N-oxides from the reaction of quinoline N-oxides with α-diketonesviaC–C bond cleavage was developed. A variety of quinoline N-oxides and α-diketones with different groups was well tolerated in this system.

16

Park, Ji Eun, and Youn K. Kang. "Evidence of a Wheland Intermediate in Carboxylate-Assisted C(sp2)−H Activation by Pd(IV) Active Catalyst Species Studied via DFT Calculations." Catalysts 13, no. 4 (April 11, 2023): 724. http://dx.doi.org/10.3390/catal13040724.

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Evidence of a Wheland intermediate in carboxylate-assisted C−H activation was found using DFT calculations when the Pd(IV) catalyst species was postulated as the active catalyst species (ACS). In order to delineate the reaction mechanism of Pd-catalyzed bisarylation of 3-alkylbenzofuran, five hypothetical catalyst species, [Pd(OAc)(PMe3)(Ph)] (I), [Pd(OAc)2] (II), [Pd(OAc)2(PMe3)] (III), [Pd(OAc)2(Ph)]+ (IV) and [Pd(OAc)2(PMe3)(Ph)]+ (V) were tested as potential ACS candidates. The catalyst species I, previously reported as an ACS in the context of ambiphilic metal−ligand assistance or a concerted metalation-deprotonation mechanism, was unsuccessful, with maximum activation barriers (ΔG‡max) for the C(sp2)−H and C(sp3)−H activations of 33.3 and 51.4 kcal/mol, respectively. The ΔG‡max values for the C(sp2)−H and C(sp3)−H activations of II−V were 23.8/28.7, 32.0/49.6, 10.9/10.9, and 36.0/36.0 kcal/mol, respectively, indicating that ACS is likely IV. This catalyst species forms an intermediate state (IV_1) before proceeding to the transition state (IV_TS1,2) for C(sp2)−H activation, in which C(2) atom of 3-methylbenzofuran has a substantial σ-character. The degree of σ-character of the IV_1 state was further evaluated quantitatively in terms of geometric parameters, partial charge distribution, and activation strain analysis. The analysis results support the existence of a Wheland intermediate, which has long been recognized as the manifestation of the electrophilic aromatic substitution mechanism yet never been identified computationally.

17

Wang, Xiao, Ming-Zhu Lu, and Teck-Peng Loh. "Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond Activation." Catalysts 13, no. 2 (February 17, 2023): 438. http://dx.doi.org/10.3390/catal13020438.

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Macrocycles are commonly synthesized via late-stage macrolactamization and macrolactonization. Strategies involving C–C bond macrocyclization have been reported, and examples include the transition-metal-catalyzed ring-closing metathesis and coupling reactions. In this mini-review, we summarize the recent progress in the direct synthesis of polyketide and polypeptide macrocycles using a transition-metal-catalyzed C–H bond activation strategy. In the first part, rhodium-catalyzed alkene–alkene ring-closing coupling for polyketide synthesis is described. The second part summarizes the synthesis of polypeptide macrocycles. The activation of indolyl and aryl C(sp2)–H bonds followed by coupling with various coupling partners such as aryl halides, arylates, and alkynyl bromide is then documented. Moreover, transition-metal-catalyzed C–C bond macrocyclization reactions via alkyl C(sp3)–H bond activation are also included. We hope that this mini-review will inspire more researchers to explore new and broadly applicable strategies for C–C bond macrocyclization via intramolecular C–H activation.

18

Valentini, Federica, Oriana Piermatti, and Luigi Vaccaro. "Metal and Metal Oxide Nanoparticles Catalyzed C–H Activation for C–O and C–X (X = Halogen, B, P, S, Se) Bond Formation." Catalysts 13, no. 1 (December 22, 2022): 16. http://dx.doi.org/10.3390/catal13010016.

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The direct functionalization of an inactivated C–H bond has become an attractive approach to evolve toward step-economy, atom-efficient and environmentally sustainable processes. In this regard, the design and preparation of highly active metal nanoparticles as efficient catalysts for C–H bond activation under mild reaction conditions still continue to be investigated. This review focuses on the functionalization of un-activated C(sp3)–H, C(sp2)–H and C(sp)–H bonds exploiting metal and metal oxide nanoparticles C–H activation for C–O and C–X (X = Halogen, B, P, S, Se) bond formation, resulting in more sustainable access to industrial production.

19

Zucca, Antonio, Sergio Stoccoro, Maria Agostina Cinellu, Giovanni Minghetti, and Mario Manassero. "Cyclometallated derivatives of rhodium(III). Activation of C(sp3)–H vs. C(sp2)–H bonds." Journal of the Chemical Society, Dalton Transactions, no. 19 (1999): 3431–37. http://dx.doi.org/10.1039/a903614h.

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20

Prajapati, Ramanand, Ajay Kant Gola, Amrendra Kumar, Shubham Jaiswal, and Narender Tadigoppula. "o-Acetoxylation of oxo-benzoxazines via C–H activation by palladium(ii)/aluminium oxide." New Journal of Chemistry 46, no. 12 (2022): 5719–24. http://dx.doi.org/10.1039/d2nj00134a.

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21

Maraswami, Manikantha, and Teck-Peng Loh. "Transition-Metal-Catalyzed Alkenyl sp2 C–H Activation: A Short Account." Synthesis 51, no. 05 (January 23, 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 Concept4 Other Alkene Derivatives5 Intramolecular C–H Activation6 Conclusion and Future Projects

22

Uttry, Alexander, and Manuel van Gemmeren. "Direct C(sp3)–H Activation of Carboxylic Acids." Synthesis 52, no. 04 (October 17, 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 aliphatic carboxylic acids in C–H-activation-based transformations.1 Introduction2 Challenges in the C(sp3)–H Bond Activation of Carboxylic Acids3 The Lactonization of Aliphatic Carboxylic Acids4 The Directing Group Approach5 The Direct C–H Arylation of Aliphatic Carboxylic Acids6 The Direct C–H Olefination of Aliphatic Carboxylic Acids7 The Direct C–H Acetoxylation of Aliphatic Carboxylic Acids8 Summary

23

Bettadapur, Kiran R., Veeranjaneyulu Lanke, and Kandikere Ramaiah Prabhu. "A deciduous directing group approach for the addition of aryl and vinyl nucleophiles to maleimides." Chemical Communications 53, no. 46 (2017): 6251–54. http://dx.doi.org/10.1039/c7cc02392h.

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A Rh(iii)-catalyzed C–H activation followed by conjugate addition to maleimides, using carboxylic acid as a traceless/deciduous directing group, to formally furnish a C_sp2–C_sp3 bond is presented.

24

Liu, Weidong, Qingzhen Yu, Le'an Hu, Zenghua Chen, and Jianhui Huang. "Modular synthesis of dihydro-isoquinolines: palladium-catalyzed sequential C(sp2)–H and C(sp3)–H bond activation." Chemical Science 6, no. 10 (2015): 5768–72. http://dx.doi.org/10.1039/c5sc01482d.

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An efficient synthesis of dihydro-isoquinolines via a Pd–catalyzed double C–H bond activation/annulation featuring a short reaction time, high atom economy and the formation of a sterically less favoured tertiary C–N bond.

25

Seth, Kapileswar, Manesh Nautiyal, Priyank Purohit, Naisargee Parikh, and Asit K. Chakraborti. "Palladium catalyzed Csp2–H activation for direct aryl hydroxylation: the unprecedented role of 1,4-dioxane as a source of hydroxyl radicals." Chemical Communications 51, no. 1 (2015): 191–94. http://dx.doi.org/10.1039/c4cc06864e.

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26

Verma, Ashish Kumar, Ande Chennaiah, Sateesh Dubbu, and Yashwant D. Vankar. "Palladium catalyzed synthesis of sugar-fused indolines via C(sp2)–H/N H activation." Carbohydrate Research 473 (February 2019): 57–65. http://dx.doi.org/10.1016/j.carres.2018.12.015.

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27

Klare, Hendrik F. T. "Catalytic C–H Arylation of Unactivated C–H Bonds by Silylium Ion-Promoted C(sp2)–F Bond Activation." ACS Catalysis 7, no. 10 (September 20, 2017): 6999–7002. http://dx.doi.org/10.1021/acscatal.7b02658.

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28

Cheng, Huiling, Yubo Jiang, Jianhua Yang, Fen Zhao, Yaowen Liu, and Fang Luo. "Selective Diacetoxylation of Disubstituted 1,2,3-Triazoles through Palladium-Catalyzed C–H Activation." Synlett 29, no. 10 (April 12, 2018): 1373–78. http://dx.doi.org/10.1055/s-0036-1591564.

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A simple and efficient selective diacetoxylation of 1,4-disubstituted 1,2,3-triazoles by Pd-catalyzed C–H bond activation is described. PhI(OAc)2 was used as an acetyloxy source to convert aromatic sp2 C–H bonds into C–O bonds with high selectivity by employing a 1,2,3-triazole ring as an elegant directing group. A range of 1,2,3-triazoles bearing two acetyloxy groups can be readily synthesized by the reaction.

29

Liu, Yunqi, Yudong Yang, Chunxia Wang, Zhishuo Wang, and Jingsong You. "Rhodium(iii)-catalyzed regioselective oxidative annulation of anilines and allylbenzenes via C(sp3)–H/C(sp2)–H bond cleavage." Chemical Communications 55, no. 8 (2019): 1068–71. http://dx.doi.org/10.1039/c8cc09099h.

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As a proof-of-concept, we disclose the rhodium-catalyzed oxidative annulation of anilines with allylbenzenes to afford a variety of indoles, in which the allylic C(sp³)–H activation and directed C(sp²)–H activation are merged into a single approach for the first time.

30

Zhang, Yanghui, and Bin Wan. "Synthesis of Unsymmetrically Substituted Tetraphenylenes through Palladium-Catalyzed C(sp2)–H Activation." Synthesis 53, no. 18 (March 8, 2021): 3299–306. http://dx.doi.org/10.1055/a-1416-9737.

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AbstractAn efficient protocol for the palladium-catalyzed cross-coupling reaction of 2-iodobiphenyls with biphenylene has been developed through C–H activation. The reaction provides a simple and efficient method for the synthesis of unsymmetrically substituted tetraphenylenes.

31

Curto, John M., and Marisa C. Kozlowski. "Chemoselective Activation of sp3 vs sp2 C–H Bonds with Pd(II)." Journal of the American Chemical Society 137, no. 1 (December 29, 2014): 18–21. http://dx.doi.org/10.1021/ja5093166.

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32

Li, Bin, and Pierre H. Dixneuf. "sp2 C–H bond activation in water and catalytic cross-coupling reactions." Chemical Society Reviews 42, no. 13 (2013): 5744. http://dx.doi.org/10.1039/c3cs60020c.

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33

Song, Juan, Yali Li, Wei Sun, Chenglong Yi, Hao Wu, Haotian Wang, Keran Ding, Kang Xiao, and Chao Liu. "Efficient palladium-catalyzed C(sp2)–H activation towards the synthesis of fluorenes." New Journal of Chemistry 40, no. 11 (2016): 9030–33. http://dx.doi.org/10.1039/c6nj02033j.

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34

Dai, Hui-Xiong, Ming Shang, Shang-Zheng Sun, Hong-Li Wang, and Ming-Ming Wang. "Recent Progress on Copper-Mediated Directing-Group-Assisted C(sp2)–H Activation." Synthesis 48, no. 24 (September 9, 2016): 4381–99. http://dx.doi.org/10.1055/s-0035-1562795.

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35

Kathiravan, Subban, and Ian A. Nicholls. "Cobalt Catalyzed, Regioselective C(sp2)–H Activation of Amides with 1,3-Diynes." Organic Letters 19, no. 18 (August 28, 2017): 4758–61. http://dx.doi.org/10.1021/acs.orglett.7b02119.

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Gu, Zheng-Yang, Cheng-Guo Liu, Shun-Yi Wang, and Shun-Jun Ji. "Cobalt-Catalyzed Annulation of Amides with Isocyanides via C(sp2)–H Activation." Journal of Organic Chemistry 82, no. 4 (February 8, 2017): 2223–30. http://dx.doi.org/10.1021/acs.joc.6b02797.

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37

Tian, Qingshan, Xianmin Chen, Wei Liu, Zechao Wang, Suping Shi, and Chunxiang Kuang. "Regioselective halogenation of 2-substituted-1,2,3-triazoles via sp2 C–H activation." Organic & Biomolecular Chemistry 11, no. 45 (2013): 7830. http://dx.doi.org/10.1039/c3ob41558a.

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38

Wang, Yong, and Qiang Zhu. "Palladium(II)-Catalyzed Cycloamidination via C(sp2)H Activation and Isocyanide Insertion." Advanced Synthesis & Catalysis 354, no. 10 (June 29, 2012): 1902–8. http://dx.doi.org/10.1002/adsc.201200106.

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Tang, Ren-Jin, Cui-Ping Luo, Luo Yang, and Chao-Jun Li. "Rhodium(III)-Catalyzed C(sp2)H Activation and Electrophilic Amidation withN-Fluorobenzenesulfonimide." Advanced Synthesis & Catalysis 355, no. 5 (February 22, 2013): 869–73. http://dx.doi.org/10.1002/adsc.201201133.

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40

Cizikovs, Aleksandrs, and Liene Grigorjeva. "Co(III) Intermediates in Cobalt-Catalyzed, Bidentate Chelation Assisted C(sp2)-H Functionalizations." Inorganics 11, no. 5 (April 29, 2023): 194. http://dx.doi.org/10.3390/inorganics11050194.

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The C-H bond activation and functionalization is a powerful tool that provides efficient access to various organic molecules. The cobalt-catalyzed oxidative C-H bond activation and functionalization has earned enormous interest over the past two decades. Since then, a wide diversity of synthetic protocols have been published for C-C, C-Het, and C-Hal bond formation reactions. To gain some insights into the reaction mechanism, the authors performed a series of experiments and collected evidence. Several groups have successfully isolated reactive Co(III) intermediates to elucidate the reaction mechanism. In this review, we will summarize information concerning the isolated and synthesized Co(III) intermediates in cobalt-catalyzed, bidentate chelation assisted C-H bond functionalization and their reactivity based on the current knowledge about the general reaction mechanism.

41

Pashazadeh, Rahim, Saideh Rajai-Daryasarei, Siyavash Mirzaei, Mehdi Soheilizad, Samira Ansari, and Meisam Shabanian. "A Regioselective Approach to C3-Aroylcoumarins via Cobalt-Catalyzed C(sp2)–H Activation Carbonylation of Coumarins." Synthesis 51, no. 15 (April 2, 2019): 3014–20. http://dx.doi.org/10.1055/s-0037-1610702.

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A new cobalt-catalyzed C–H bond activation of coumarins with aryl halides or pseudohalides and carbon monoxide insertion to give various 3-aroylcoumarin derivatives is described. It is the first time that CO as C1 feedstock is used as the coupling partners in cobalt-catalyzed regioselective coumarin C–H functionalization reactions. Upon activation with manganese powder, the Co catalyzes the C–H bond activation carbonylation reactions of aryl iodides, bromides, and even triflates under mild conditions, providing the regioselective aroylated products in moderate to good yields.

42

Swamy, V. S. V. S. N., Nasrina Parvin, K. Vipin Raj, Kumar Vanka, and Sakya S. Sen. "C(sp3)–F, C(sp2)–F and C(sp3)–H bond activation at silicon(ii) centers." Chemical Communications 53, no. 71 (2017): 9850–53. http://dx.doi.org/10.1039/c7cc05145j.

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Silylene, [PhC(NtBu)₂SiN(SiMe₃)₂] (1) underwent C(sp³)–F, C(sp²)–F and C(sp³)–H bond activation with trifluoroacetophenone, octafluorotoluene, and acetophenone, respectively, under ambient conditions.

43

Fujihara, Tetsuaki, Yutaka Tanji, and Yasushi Tsuji. "Palladium-Catalyzed Synthesis of Fluorenes by Intramolecular C(sp2)–H Activation at Room Temperature." Synlett 31, no. 08 (February 4, 2020): 805–8. http://dx.doi.org/10.1055/s-0039-1690812.

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The synthesis of fluorenes by intramolecular Pd-catalyzed C(sp2)–H activation of 2-arylbenzyl chlorides was conducted at room temperature by using commercially available triphenylphosphine and pivalic acid as ligands. The desired reactions proceeded efficiently at room temperature, and various substrates were converted into the corresponding fluorene derivatives in excellent yields.

44

Konwar, Manashjyoti, Roktopol Hazarika, and Diganta Sarma. "Synthetic advances in C(sp2)-H/N–H arylation of pyrazole derivatives through activation/substitution." Tetrahedron 102 (December 2021): 132504. http://dx.doi.org/10.1016/j.tet.2021.132504.

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45

Young, Michael, Mohit Kapoor, Pratibha Chand-Thakuri, Justin Maxwell, Daniel Liu, and Hanyang Zhou. "Carbon Dioxide-Driven Palladium-Catalyzed C–H Activation of Amines: A Unified Approach for the Arylation of Aliphatic and Aromatic Primary and Secondary Amines." Synlett 30, no. 05 (January 8, 2019): 519–24. http://dx.doi.org/10.1055/s-0037-1611381.

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Abstract:

Amines are an important class of compounds in organic chemistry and serve as an important motif in various industries, including pharmaceuticals, agrochemicals, and biotechnology. Several methods have been developed for the C–H functionalization of amines using various directing groups, but functionalization of free amines remains a challenge. Here, we discuss our recently developed carbon dioxide driven highly site-selective γ-arylation of alkyl- and benzylic amines via a palladium-catalyzed C–H bond-activation process. By using carbon dioxide as an inexpensive, sustainable, and transient directing group, a wide variety of amines were arylated at either γ-sp3 or sp2 carbon–hydrogen bonds with high selectivity based on substrate and conditions. This newly developed strategy provides straightforward access to important scaffolds in organic and medicinal chemistry without the need for any expensive directing groups.1 Introduction2 C(sp3)–H Arylation of Aliphatic Amines3 C(sp2)–H Arylation of Benzylamines4 Mechanistic Questions5 Future Outlook

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Zhou, Wei, Hongji Li, and Lei Wang. "Direct Carbo-Acylation Reactions of 2-Arylpyridines with α-Diketones via Pd-Catalyzed C–H Activation and Selective C(sp2)–C(sp2) Cleavage." Organic Letters 14, no. 17 (August 27, 2012): 4594–97. http://dx.doi.org/10.1021/ol3020557.

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Kim, Daeun, Geunho Choi, Weonjeong Kim, Dongwook Kim, Youn K. Kang, and Soon Hyeok Hong. "The site-selectivity and mechanism of Pd-catalyzed C(sp2)–H arylation of simple arenes." Chemical Science 12, no. 1 (2021): 363–73. http://dx.doi.org/10.1039/d0sc05414c.

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Li, Dan-Dan, Yi-Xuan Cao, and Guan-Wu Wang. "Palladium-catalyzed ortho-acyloxylation of N-nitrosoanilines via direct sp2 C–H bond activation." Organic & Biomolecular Chemistry 13, no. 25 (2015): 6958–64. http://dx.doi.org/10.1039/c5ob00691k.

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Abstract:

The palladium-catalyzed N-nitroso-directed ortho-acyloxylation of N-nitrosoanilines has been demonstrated via sp² C–H activation with PhI(OAc)₂ as the oxidant and Ac₂O/AcOH (1 : 1) or C₂H₅CO₂H as the reaction medium.

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Arevalo, Rebeca, Tyler P. Pabst, and Paul J. Chirik. "C(sp2)–H Borylation of Heterocycles by Well-Defined Bis(silylene)pyridine Cobalt(III) Precatalysts: Pincer Modification, C(sp2)–H Activation, and Catalytically Relevant Intermediates." Organometallics 39, no. 14 (July 8, 2020): 2763–73. http://dx.doi.org/10.1021/acs.organomet.0c00382.

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Hu, Zhe-Yao, Yan Zhang, Xin-Chang Li, Jing Zi, and Xun-Xiang Guo. "Pd-Catalyzed Intramolecular Chemoselective C(sp2)–H and C(sp3)–H Activation of N-Alkyl-N-arylanthranilic Acids." Organic Letters 21, no. 4 (January 29, 2019): 989–92. http://dx.doi.org/10.1021/acs.orglett.8b03976.

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Journal articles on the topic 'Activation de la liaison C(sp2)-H'

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