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Journal articles on the topic 'C(sp2)-H bond activation'

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Author: Grafiati

Published: 25 May 2024

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1

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.

2

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.

3

Paira, Moumita. "Recent Developments of Palladium-Catalyzed C(sp3)/C(sp2)-H Bond Functionalizations Assisted by 8-Aminoquinoline Bidentate Directing Group." Asian Journal of Chemistry 34, no. 8 (2022): 1958–74. http://dx.doi.org/10.14233/ajchem.2022.23774.

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Recently growing demand for cleaner, direct even more regioselective reaction sequences, the formation of carbon-carbon or carbon-heteroatom bonds through C-H activation has developed as a unique methodology. Since the pioneering work of Daugulis on the use of the 8-aminoquinoline auxiliaries as removable bidentate directing groups in palladium-catalyzed C-H bond activations has emerged as a ground breaking strategy for the construction of carbon-carbon or carbon-heteroatom bonds. Hence, this review intends to cover most of the recent advances on 8-aminoquinoline directed palladium-catalyzed C(sp3)/C(sp2)–H bonds functionalizations and highlighted the synthesis of C-branched glycosides.

4

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.

5

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.

6

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.

7

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.

8

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.

9

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.

10

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.

11

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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12

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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13

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.

14

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.

15

Abdelmalek, Fatiha, Fazia Derridj, Safia Djebbar, Jean-François Soulé, and Henri Doucet. "Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp2)–H bond arylations." Beilstein Journal of Organic Chemistry 11 (October 28, 2015): 2012–20. http://dx.doi.org/10.3762/bjoc.11.218.

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We report herein a two or three step synthesis of fluorinated π-conjugated oligomers through iterative C–H bond arylations. Palladium-catalyzed desulfitative arylation of heteroarenes allowed in a first step the synthesis of fluoroaryl-heteroarene units in high yields. Then, the next steps involve direct arylation with aryl bromides catalyzed by PdCl(C3H5)(dppb) to afford triad or tetrad heteroaromatic compounds via regioselective activation of C(sp2)–H bonds.

16

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.

17

Xu, Runsheng, Yueer Zhu, Feixiang Xiong, and Suli Tong. "Direct Sulfoxidation of Aromatic Methyl Thioethers with Aryl Halides by Copper-Catalyzed C(sp3)–H Bond Activation." Catalysts 9, no. 1 (January 21, 2019): 105. http://dx.doi.org/10.3390/catal9010105.

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A copper-catalyzed direct sulfoxidation reaction by C(sp3)–H bond activation has been developed. Starting from sample aromatic methyl thioethers with aryl halides, versatile biologically-active arylbenzylsulfoxide derivatives were efficiently synthesized in good to high yields under mild conditions. This new methodology provides an economical approach toward C(sp3)–C(sp2) bond formation.

18

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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19

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.

20

Yamaoka, Yousuke, and Hideto Miyabe. "NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation." Catalysts 14, no. 4 (March 22, 2024): 219. http://dx.doi.org/10.3390/catal14040219.

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In the past few decades, N-heterocyclic carbenes (NHCs) have opened the new field of organocatalysis in synthetic organic chemistry. This review highlights the dramatic progress in the field of NHC-catalyzed C–O bond formation based on the activation of aldehyde C(sp2)–H bonds. The oxidative and redox transformations for the synthesis of various molecules with structural diversity and complexity are summarized. Furthermore, new methods and strategies for NHC catalysis are emerging continuously; thus, cooperative catalysis with Brønsted acid, hydrogen-bonding catalyst, transition-metal catalyst, and photocatalyst are also described.

21

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.

22

Cui, Bingcun, Guosheng Huang, Jin Liu, Shaofen Jin, Yingxing Zhou, Dongmei Ni, Tingting Liu, Gang Hu, and Xin Yu. "Palladium-Catalyzed ortho-Monoacylation of Arenes with Aldehydes via 1,2,4-Benzotriazine-Directed C–H Bond Activation." Synthesis 52, no. 09 (February 10, 2020): 1407–16. http://dx.doi.org/10.1055/s-0039-1691564.

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An efficient palladium-catalyzed C–H bond functionalization/ortho-monoacylation reaction of 3-aryl-1,2,4-benzotriazines with (hetero)aryl or alkyl aldehydes has been developed, which offers a facile and alternative strategy for direct modification and further diversification of 3-aryl-1,2,4-benzotriazines. Bioactive 1,2,4-benzotriazine has been employed as a novel directing group for the palladium-catalyzed regioselective monoacylation of sp2 C–H bond protocol with broad substrate scope and good functional group tolerance.

23

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.

24

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

25

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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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

26

Sharma, Satyasheel, Neeraj Kumar Mishra, Youngmi Shin, and In Su Kim. "Transition-Metal-Catalyzed Oxidative and Decarboxylative Acylations through sp2 C-H Bond Activation." Current Organic Chemistry 20, no. 5 (December 3, 2015): 471–511. http://dx.doi.org/10.2174/1385272819666150122234834.

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27

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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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.

28

Zhang, Zhiguo, Jingjing Qian, Guisheng Zhang, Nana Ma, Qingfeng Liu, Tongxin Liu, Kai Sun, and Lei Shi. "Copper(i) catalyzed C(sp2)–N bond formation: synthesis of pyrrolo[3,2-c]quinolinone derivatives." Organic Chemistry Frontiers 3, no. 3 (2016): 344–48. http://dx.doi.org/10.1039/c5qo00417a.

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An intramolecular copper-catalyzed direct C(sp²)–H activation/C(sp²)–N bond formation reaction has been developed for the synthesis of pyrrolo[3,2-c]quinolinone derivatives under an oxygen atmosphere. This approach presents an alternative route to the tricyclic core of martinellic acid or martinelline.

29

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

30

Mao, Jiangang, and Weiliang Bao. "Palladium-catalyzed [2+1+1] annulation of norbornenes with (z)-bromostyrenes: synthesis of bismethylenecyclobutanes via twofold C(sp2)–H bond activation." Chem. Commun. 50, no. 99 (2014): 15726–29. http://dx.doi.org/10.1039/c4cc06545j.

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A Pd(0)-catalyzed domino bismethylenecyclobutanation reaction was established. The [2+1+1] cycloaddition involves twofold C(sp²)–H bond activation and formation of three carbon–carbon bonds.

31

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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32

Yuan, Yizhi, Song Song, and Ning Jiao. "Recent Development in Pd-Catalyzedmeta-C(sp2)-H Bond Activation Based on Directing Strategy." Acta Chimica Sinica 73, no. 12 (2015): 1231. http://dx.doi.org/10.6023/a15050319.

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33

Nan, Jiang, Zhijun Zuo, Lei Luo, Lu Bai, Huayu Zheng, Yini Yuan, Jingjing Liu, Xinjun Luan, and Yaoyu Wang. "RuII-Catalyzed Vinylative Dearomatization of Naphthols via a C(sp2)–H Bond Activation Approach." Journal of the American Chemical Society 135, no. 46 (November 6, 2013): 17306–9. http://dx.doi.org/10.1021/ja410060e.

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34

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.

35

Naveen, Kanagaraj, Avanashiappan Nandakumar, and Paramasivan Perumal. "Synthesis of 4-Alkylidene-Substituted 1,2,3,4-Tetrahydroisoquinolines via Palladium-Catalyzed Carbopalladation/C–H Activation of 2-Bromobenzyl-N-propargylamines." Synthesis 47, no. 11 (March 18, 2015): 1633–42. http://dx.doi.org/10.1055/s-0034-1380414.

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Tetrasubstituted alkene-based 1,2,3,4-tetrahydroisoquinolines are synthesized via the formation of a cyclic carbopalladation complex followed by C–H bond activation of the sp2 carbon in arenes. This domino reaction proceeds with good selectivity and provides good yields of the products. The requisite starting materials are synthesized by copper(I) iodide catalyzed A3-coupling reactions.

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Lin, Yumei, Hui Xu, Lei Gong, Ting Bin Wen, Xu-Min He, and Haiping Xia. "C−H Bond Activation and Subsequent C(sp2)−C(sp3) Bond Formation: Coupling of Bromomethyl and Triphenylphosphine in an Iridium Complex." Organometallics 29, no. 13 (July 12, 2010): 2904–10. http://dx.doi.org/10.1021/om100187t.

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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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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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Mondal, Biplab, and Brindaban Roy. "Di-tert-butyl peroxide (DTBP) promoted dehydrogenative coupling: an expedient and metal-free synthesis of oxindoles via intramolecular C(sp2)–H and C(sp3)–H bond activation." RSC Advances 5, no. 85 (2015): 69119–23. http://dx.doi.org/10.1039/c5ra09055e.

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Abstract:

An efficient di-tert-butyl peroxide (DTBP) promoted synthesis of oxindole has been developed. This methodology involves C(sp³)–H and C(sp²)–H bond activation under metal-free conditions.

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Shi, Yun, Meng-Sheng Li, Fangdong Zhang, and Baohua Chen. "Nickel(ii)-catalyzed tandem C(sp2)–H bond activation and annulation of arenes with gem-dibromoalkenes." RSC Advances 8, no. 50 (2018): 28668–75. http://dx.doi.org/10.1039/c8ra03278e.

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A nickel(ii)/silver(i)-catalyzed tandem C(sp²)–H activation and intramolecular annulation of arenes with dibromoalkenes has been successfully achieved, which offers an efficient approach to the 3-methyleneisoindolin-1-one scaffold.

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Zhang, Chun, Jing Ji, and Peipei Sun. "Palladium-Catalyzed Alkenylation via sp2 C–H Bond Activation Using Phenolic Hydroxyl as the Directing Group." Journal of Organic Chemistry 79, no. 7 (March 20, 2014): 3200–3205. http://dx.doi.org/10.1021/jo4028825.

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Nan, Jiang, Zhijun Zuo, Lei Luo, Lu Bai, Huayu Zheng, Yini Yuan, Jingjing Liu, Xinjun Luan, and Yaoyu Wang. "ChemInform Abstract: RuII-Catalyzed Vinylative Dearomatization of Naphthols via a C(sp2)-H Bond Activation Approach." ChemInform 45, no. 23 (May 22, 2014): no. http://dx.doi.org/10.1002/chin.201423075.

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Shen, Guodong, Lingyu Zhao, Yichen Wang, Wenfang Xia, Mingsen Yang, and Tongxin Zhang. "Palladium–copper catalyzed C(sp3)–C(sp2) bond C–H activation cross-coupling reaction: selective arylation to synthesize 9-aryl-9H-xanthene and 9,9-diaryl-xanthene derivatives." RSC Advances 6, no. 88 (2016): 84748–51. http://dx.doi.org/10.1039/c6ra17546e.

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A novel palladium–copper catalyzed C(sp³)–C(sp²) bond C–H activation cross-coupling reaction has been developed. A series of 9-aryl-9H-xanthenes and 9,9-diaryl-xanthenes were selectively synthesized in moderate to good yields by controlling the reaction time and temperature.

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Monsigny, Louis, Floriane Doche, and Tatiana Besset. "Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview." Beilstein Journal of Organic Chemistry 19 (April 17, 2023): 448–73. http://dx.doi.org/10.3762/bjoc.19.35.

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The last decade has witnessed the emergence of innovative synthetic tools for the synthesis of fluorinated molecules. Among these approaches, the transition-metal-catalyzed functionalization of various scaffolds with a panel of fluorinated groups (XRF, X = S, Se, O) offered straightforward access to high value-added compounds. This review will highlight the main advances made in the field with the transition-metal-catalyzed functionalization of C(sp2) and C(sp3) centers with SCF3, SeCF3, or OCH2CF3 groups among others, by C–H bond activation. The scope and limitations of these transformations are discussed in this review.

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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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Carr, Kevin J. T., David L. Davies, Stuart A. Macgregor, Kuldip Singh, and Barbara Villa-Marcos. "Metal control of selectivity in acetate-assisted C–H bond activation: an experimental and computational study of heterocyclic, vinylic and phenylic C(sp2)–H bonds at Ir and Rh." Chem. Sci. 5, no. 6 (2014): 2340–46. http://dx.doi.org/10.1039/c4sc00738g.

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Experimental and DFT studies show the selectivity of C–H bond activation at [MCl₂Cp*]₂ (M = Ir, Rh) species can be controlled by the choice of metal catalyst, reflecting kinetic control at M = Ir and thermodynamic control at M = Rh.

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Yadav, Lalit, Mohit K. Tiwari, Bharti Rajesh Kumar Shyamlal, and Sandeep Chaudhary. "Organocatalyst in Direct C(sp2)–H Arylation of Unactivated Arenes: [1-(2-Hydroxyethyl)-piperazine]-Catalyzed Inter-/Intra-molecular C–H Bond Activation." Journal of Organic Chemistry 85, no. 12 (May 22, 2020): 8121–41. http://dx.doi.org/10.1021/acs.joc.0c01019.

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Ding, Jun, Ying Guo, Ling-Yan Shao, Fei-Yi Zhao, Dao-Hua Liao, Hong-Wei Liu, and Ya-Fei Ji. "Palladium-catalyzed multi-acetoxylation of 1,3-disubstituted 1H-pyrazole-5-carboxylates via direct C(sp2)H or C(sp3)H bond activation." Chinese Chemical Letters 27, no. 10 (October 2016): 1617–21. http://dx.doi.org/10.1016/j.cclet.2016.04.007.

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Eom, Dahan, Yeonseok Jeong, Yea Rin Kim, Euichul Lee, Wonseok Choi, and Phil Ho Lee. "Palladium-Catalyzed C(sp2 and sp3)–H Activation/C–O Bond Formation: Synthesis of Benzoxaphosphole 1- and 2-Oxides." Organic Letters 15, no. 20 (October 8, 2013): 5210–13. http://dx.doi.org/10.1021/ol402736v.

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Bunescu, Ala, Tiffany Piou, Qian Wang, and Jieping Zhu. "Pd-Catalyzed Dehydrogenative Aryl–Aryl Bond Formation via Double C(sp2)–H Bond Activation: Efficient Synthesis of [3,4]-Fused Oxindoles." Organic Letters 17, no. 2 (December 19, 2014): 334–37. http://dx.doi.org/10.1021/ol503442n.

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