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非手性C-H键活化综述

October,27, 2021

非手性C-H键活化综述

1) J. Thongpaen, R. Manguin, O. Baslé, Angew. Chem. Int. Ed. 2020, 59, 10242.

Chiral N-Heterocyclic Carbene Ligands Enable Asymmetric C−H Bond Functionalization  


2) Q. Zhao, G. Meng, S. P. Nolan, and M. Szostak, Chem. Rev.2020, 120 (4), 1981-2048.

N-Heterocyclic Carbene Complexes in C–H Activation Reactions


3) Gang Liao, Tao Zhang, Zhi-Keng Lin, and Bing-Feng Shi, Angew. Chem. Int. Ed. 2020, 59, 2–6.

Transition Metal-Catalyzed Enantioselective C-H Functionalization via Chiral Transient Directing Group Strategies


4) Bijin Li, Ahmed I.M. Ali, Haibo Ge, Chem. 2020, 6, 2591-2657.

Recent Advances in Using Transition-Metal-Catalyzed C–H Functionalization to Build Fluorescent Materials


5) Geetika Rani, Vijay Luxami and Kamaldeep Paul, Chem. Commun. 2020, 56, 12479-12521.

Traceless Directing Groups: a Novel Strategy in Regiodivergent C–H Functionalization


6) Jayabrata Das, Srimanta Guin and Debabrata Maiti, Chem. Sci. 2020, 11, 10887-10909.

Diverse Strategies for Transition Metal Catalyzed Distal C(sp3)–H Functionalizations


7) Pu-Sheng Wang and Liu-Zhu Gong, Acc. Chem. Res. 2020, 53, 2841–2854.

Palladium-Catalyzed Asymmetric Allylic C−H Functionalization: Mechanism, Stereo- and Regioselectivities, and Synthetic Applications


8) N. Y. S. Lam, K. Wu, J.-Q. Yu, Angew. Chem. Int. Ed. 2021, 60, 15767.

Advancing the Logic of Chemical Synthesis: C−H Activation as Strategic and Tactical Disconnections for C−C Bond Construction


9) Maria I. Lapuh, Sara Mazeh, and Tatiana Besset, ACS Catal. 2020, 10, 12898–12919.

Chiral Transient Directing Groups in Transition-Metal-Catalyzed Enantioselective C–H Bond Functionalization


10) Bei-Bei Zhan,a Meng-Xue Jiangb and Bing-Feng Shi, Chem. Commun., 2020, 56, 13950-13958.

Late-stage Functionalization of Peptides via a Palladium-Catalyzed C(sp3)–H Activation Strategy


11) Youai Qiu , Cuiju Zhu , Maximilian Stangier, Julia Struwe & Lutz Ackermann, CCS Chem. 2020, 2, 1529–1552.

Rhodaelectro-Catalyzed C–H and C–C Activation


12) Jianchun Wang and Guangbin Dong, Chem. Rev. 2019, 119, 7478−7528. 

Palladium/Norbornene Cooperative Catalysis


13) Hong-Gang Cheng, Shuqing Chen, Ruiming Chen, and Qianghui Zhou, Angew. Chem. Int. Ed. 2019, 58, 5832–5844.

Palladium(II)-Initiated Catellani-Type Reactions


14) Rémi Blieck, Marc Taillefer and Florian Monnier, Chem. Rev. 2020, 120, 13545–13598.

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C−N, C−C, and C−O Bonds


15) Qi Zhang and Bing-Feng Shi, Chem. Sci., 2021, 12, 841-852.

Site-selective functionalization of remote aliphatic C–H bonds via C–H metallation


16) Yongjie Wu, Bingfeng Shi, Chin. J. Org. Chem. 2020, 40, 3517-3535.

Transition Metal-Catalyzed C—H Activation via Imine-Based Transient Directing Group Strategy


17) Qiangsheng Sun, Wei Sun, Chin. J. Org. Chem. 2020, 40, 3686-3696.

Recent Progress in C(sp3 )—H Asymmetric Oxidation Catalyzed by Bioinspired Metal Complexes


18) Xiangyang Wang, Xuetao Xu, Zhenhua Wang, Ping Fang, Tiansheng Mei, Chin. J. Org. Chem. 2020, 40, 3738-3747.

Advances in Asymmetric Organotransition Metal-Catalyzed Electrochemistry


19) Yuhang Yang, Weiwei Gao, Yongqiang Wang, Xiaodong Wang, Fei Cao, Tao Shi, and Zhen Wang, ACS Catal. 2021, 11, 967−984.

Recent Advances in Copper Promoted Inert C(sp3 )−H Functionalization


20) Yingtao Wu, Chao Pi, Yangjie Wu and Xiuling Cui, Chem. Soc. Rev., 2021, 50, 3677-3689.

Directing group migration strategy in transition-metal-catalysed direct C–H functionalization


21) Jian Zhang, Xiunan Lu, Cong Shen, Liangyao Xu, Liyuan Ding and Guofu Zhong, Chem. Soc. Rev., 2021, 50, 3263-3314.

Recent advances in chelation-assisted site- and stereoselective alkenyl C–H functionalization


22) Jose´ A. Carmona, Carlos Rodrı´guez-Franco, Rosario Ferna´ndez, Valentı´n Hornillos and Jose´ M. Lassaletta, Chem. Soc. Rev., 2021, 50, 2968-2983.

Atroposelective transformation of axially chiral (hetero)biaryls. From desymmetrization to modern resolution strategies


23) Gang Liao, Yong-Jie Wu, Bing-Feng Shi, Acta Chim. Sinica, 2020, 78, 289-298.

Noncovalent Interaction in Transition Metal-Catalyzed Selective C-H Activation


24) Uttam Dutta, Sudip Maiti, Trisha Bhattacharya, Debabrata Maiti, Science 372, eabd5992 (2021).

Arene diversification through distal C(sp2)−H functionalization 


25) Chem. Soc. Rev., 2021, 50, 5062–5085

Metal-catalyzed silylation of sp 3 C–H bonds  


26) John C. K. Chu and Tomislav Rovis,  Angew. Chem. Int. Ed. 2018, 57, 62–101

Complementary Strategies for Directed C(sp3)−H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer 


27) Toryn Dalton, Teresa Faber, and Frank Glorius, ACS Cent. Sci. 2021, 7, 245−261

C−H Activation: Toward Sustainability and Applications


28) Ramasamy Manoharan and Masilamani Jeganmohan, Eur. J. Org. Chem. 2020, 7304–7319

Recent Advancements in Allylic C(sp 3 )–H Functionalization of Olefins Catalyzed by Rh(III) or Ir(III) Complexes


29) Sumeet Ranjan Sahoo, Subhabrata Dutta, Shaeel A. Al-Thabaiti, Mohamed Mokhtar and Debabrata Maiti, Chem. Commun., 2021, 57, 11885-11903

Transition metal catalyzed C–H bond activation by exo-metallacycle intermediates


30) Feng, Ya-Lan Shi, Bing-Feng, Chin. J. Org. Chem.2021 , 41, 3753-3770

 Recent Advances in Base Metal (Copper, Cobalt and Nickel)-Catalyzed Directed C—H Amination


31) Ming Zhang, Qiuhong Wang, Yiyuan Peng, Zhiyuan Chen, Changfeng Wan, Junmin Chen, Yongli Zhao, Rongli Zhang and Ai Qin Zhang, Chem. Commun., 2019, 55, 13048--13065

Transition metal-catalyzed sp 3 C–H activation and intramolecular C–N coupling to construct nitrogen heterocyclic scaffolds


32) Xiao-Lan Liu, Luo-Bin Jiang, Mu-Peng Luo, Zhi Ren and Shou-Guo Wang, Org. Chem. Front., 2022, 9, 265-280

Recent advances in catalytic enantioselective direct C–H bond functionalization of electron-deficient N-containing heteroarenes


33) Tobias Gensch, Michael J. James, Toryn Dalton, and Frank Glorius, Angew. Chem. Int. Ed. 2018, 57, 2296–2306

 Increasing Catalyst Efficiency in C-H ActivationCatalysis 


34) Saikat Pandit, Sudip Maiti and Debabrata Maiti, Org. Chem. Front., 2021, 8, 4349-4358.

Noncovalent interactions in Ir-catalyzed remote C–H borylation: a recent update


35) Balaji D. Barve, Yao-Haur Kuo and Wen-Tai Li, Chem. Commun., 2021, 00, 1–12.

Pd-catalyzed and ligand-enabled alkene difunctionalization via unactivated C–H bond functionalization


36) Jiang-Fei Li, Yu-Xin Luan & Mengchun Ye, . Sci China Chem, 2021, 64: 1923–1937, 

Bimetallic anchoring catalysis for C–H and C–C activation 


37) Long Zheng, Xiao-Xue Nie, Yichen Wu and Peng Wang, 10.1002/ejoc.202101084.

Construction of Si-Stereogenic Silanes through C-H Activation Approach


38) Seung Youn Hong, Yeongyu Hwang, Minhan Lee, and Sukbok Chang. Acc. Chem. Res. 2021, 54, 2683−2700

Mechanism-Guided Development of Transition-Metal-Catalyzed C−N Bond-Forming Reactions Using Dioxazolones as the Versatile Amidating Source


39) Ming-Yao Huang and Shou-Fei Zhu. DOI: 10.1039/d1sc03328j

Uncommon carbene insertion reactions 


40) Qun Zhao, Guangrong Meng, Steven P. Nolan, and Michal Szostak. Chem. Rev. 2020, 120, 1981−2048.

N‑Heterocyclic Carbene Complexes in C−H Activation Reactions.


41) Guangrong Meng, Nelson Y. S. Lam, Erika L. Lucas, Tyler G. Saint-Denis, Pritha Verma, Nikita Chekshin, and Jin-Quan Yu. J. Am. Chem. Soc. 2020, 142, 10571−10591.

Achieving Site-Selectivity for C−H Activation Processes Based on Distance and Geometry: A Carpenter’s Approach.


42) Yang Liao, Feng Liu and Zhang-jie Shi. DOI: 10.1039/d1cc04802c.

Recent progress in the oxidative coupling of unactivated Csp3 –H bonds with other C–H bonds.


43) Kangkan Talukdar, Tariq A. Shah, Tanumay Sarkar,  Subhasish Roy, Prabhat Kumar Maharana and Tharmalingam Punniyamurthy. DOI: 10.1039/d1cc05291h.

Pd-catalyzed bidentate auxiliary assisted remote C(sp3 )–H functionalization.


44) Binlin Zhao, Baskaran Prabagar, and Zhuangzhi Shi. Chem. 2021, 7,  2585–2634.

Modern strategies for C–H functionalization of heteroarenes with alternative coupling partners.


45) Bin Liu, Andrew M. Romine, Camille Z. Rubel, Keary M. Engle*, and Bing-Feng Shi*  Chem. Rev. 2021, 121, 14957−15074

Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3 )−H Bonds. 


46) Binlin Zhao, Baskaran Prabagar, and Zhuangzhi Shi.  Chem 7, 2585–2634, October 14, 2021

Modern strategies for C–H functionalization of heteroarenes with alternative coupling partners. 


47) Yuanhong Ma, Shao-Jie Lou and Zhaomin Hou.  Chem. Soc. Rev., 2021, 50, 1945-1967

Electron-deficient boron-based catalysts for C–H bond functionalisation


48) Guilherme A. M. Jardim, Renato L. de Carvalho, Mateus P. Nunes, Luana A. Machado, Leandro D. Almeida, Karim A. Bahou, John F. Bower* and Eufraˆnio N. da Silva Ju´nior. Chem. Commun., DOI:10.1039/d1cc07040a.

Looking deep into C–H functionalization: the synthesis and application of cyclopentadienyl and related metal catalysts.


49) Li Zhang and Tobias Ritter. J. Am. Chem. Soc. 2022, 144, 2399–2414.

A Perspective on Late-Stage Aromatic C−H Bond Functionalization.


50) Rajib Mandal, Bholanath Garai, and Basker Sundararaju. ACS Catal. 2022, 12, 3452−3506.

Weak-Coordination in C−H Bond Functionalizations Catalyzed by 3d Metals.


51) Arijit Saha, Majji Shankar, Somratan Sau and Akhila K. Sahoo. Chem. Commun.. DOI: 10.1039/d2cc00172a.

Multiple annulations of inert C(sp2 )–H bonds with alkynes.


52) Yuan He, Zilong Huang, Kaikai Wu, Juan Ma, Yong-Gui Zhou and Zhengkun Yu. Chem. Soc. Rev., 2022, 51, 2759–2852.

Recent advances in transition-metal-catalyzed carbene insertion to C–H bonds.


53) Daniel S. Brandes and Jonathan A. Ellman. Chem. Soc. Rev., 2022, 51, 6738–6756.

C–H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity


54) Arup Mondal, and Manuel van Gemmeren. DOI:10.1002/anie.202210825.

Silver-Free C–H Activation: Strategic Approaches towards Realizing the Full Potential of C–H Activation in Sustainable Organic Synthesis


55) Supriya Rej and Naoto Chatani. Angew. Chem. Int. Ed. 2019, 58, 8304 – 8329.

Rhodium-Catalyzed C(sp2 )- or C(sp3 )-H Bond Functionalization Assisted by Removable Directing Groups.


56) Gaurav Prakash, Nilanjan Paul, Gwyndaf A. Oliver, Daniel B. Werz and Debabrata Maiti. Chem. Soc. Rev., 2022, 51, 3123-3163.

C–H deuteration of organic compounds and potential drug candidates


57) Kongchuan Wu, Kaihong Lu, Jianbin Lin and Hui-Jun Zhang. Chin. J. Org. Chem. 2023, 43. DOI: 10.6023/cjoc202211042.

Ortho-C-H Bond Functionalization of Rylene Diimides


58) Pan Yannian, Qin Xiao, Yuan Chengkai and Lu Yi. Chin. J. Org. Chem. 2023, 43. DOI:10.6023/cjoc202211039.

Application of Ligands in Cp*Rh(III)-catalyzed C−H Bond Func tionalization Reaction


59) Sandip Kumar Das, Satyajit Roy and Buddhadeb Chattopadhyay. Angew. Chem. Int. Ed. 2023, 62, e202210912.

Transition-Metal-Catalyzed Denitrogenative Annulation to Access High-Valued N-Heterocycles


60) Rahul Keshri, Debanjan Rana, Argha Saha, Shaeel Ahmed Al-Thabaiti, Abdulmohsen Ali Alshehri, Salem M. Bawaked and Debabrata Maiti. ACS Catal. 2023, 13, 4500−4516.

Free Amine and Alcohol As the Director for Regioselective C(sp2 )−H Bond Functionalization


61) Sayan Roy, Subir Panja, Sumeet Ranjan Sahoo, Sagnik Chatterjeea and Debabrata Maiti. Chem. Soc. Rev., 2023, 10.1039/D0CS01466D.

Enroute sustainability: metal free C–H bond functionalisation


62) Baitan Chakraborty and Christine K. Luscombe. Angew. Chem. Int. Ed. 2023, e202301247.

Cross-Dehydrogenative Coupling Polymerization via C-H Activation for the Synthesisof Conjugated Polymers


63) Hui Cao, Qiang Cheng and Armido Studer. Angew. Chem. Int. Ed. 2023, e202302941.

meta-Selective C−H Functionalization of Pyridines


64) Vikash Kumar, Rajaram Maayuri, Lusina Mantry and Parthasarathy Gandeepan. Chem Asian J. 2023, e202300060.

Recent Advances in Rhodium-Catalyzed Electrochemical C-H Activation


65) Shrikant M. Khake and Naoto Chatani. Trends in Chemistry, 2019, 1, 524-539.

Chelation-Assisted Nickel-Catalyzed C−H Functionalizations


66) Parthasarathy Gandeepan and Lutz Ackermann. Chem, 2018, 4, 199–222.

Transient Directing Groups for Transformative C–H Activation by Synergistic Metal Catalysis


67) Yadagiri Kommagalla and Naoto Chatani. Coordination Chemistry Reviews, 2017, 350, 117–135.

Cobalt(II)-catalyzed CAH functionalization using an N,N0 -bidentate directing group


68) Janis Mikelis Zakis, Tomas Smejkal and Joanna Wencel-Delord. Chem. Commun., 2022, 58, 483–490.

Cyclometallated complexes as catalysts for C–H activation and functionalization


69) Kaj M. van Vliet and Bas de Bruin. ACS Catal. 2020, 10, 4751−4769.

Dioxazolones: Stable Substrates for the Catalytic Transfer of Acyl Nitrenes


70) Raju S. Thombal, Peter Yuosef M. Rubio, Daesung Lee, Debabrata Maiti and Yong Rok Lee. ACS Catal. 2022, 12, 5217−5230.

Modern Palladium-Catalyzed Transformations Involving C−H Activation and Subsequent Annulation


71) Arijit Saha, Majji Shankar, Somratan Sau and Akhila K. Sahoo. Chem. Commun., 2022, 58, 4561-4587.

Multiple annulations of inert C(sp2 )–H bonds with alkynes


72) Mar G omez-Gallego and Miguel A. Sierra. Chem. Rev. 2011, 111, 4857–4963.

Kinetic Isotope Effects in the Study ofOrganometallic ReactionMechanisms


73) Shyam Kumar Banjare, Pranav Shridhar Mahulkar, Tanmayee Nanda, Bedadyuti Vedvyas Pati,  Lamphiza O. Najiar and Ponneri C. Ravikumar. Chem. Commun., 2022,58, 10262. 

Diverse reactivity of alkynes in C–H activation reactions


74) Rui Wu, Dong Zhu and Shifa Zhu. Org. Chem. Front., 2023, 10, 2849-2878.

Dirhodium: carbene transformations and beyond


75) Wang Jiang and Zhuangzhi Shi. Chin. J. Org. Chem. 2023, 43, 1691-1705.

Recent Progress in meta-/para-Selective Aromatic C—H Borylation


76) Zhongyi Zeng, Hui Gao, Zhi Zhou and Wei Yi. ACS Catal. 2022, 12, 14754−14772.

Intermolecular Redox-Neutral Carboamination of C−C Multiple Bonds Initiated by Transition-Metal-Catalyzed C−H Activation


77) Ming-Zhu Lu, Jeffrey Goh, Manikantha Maraswami, Zhenhua Jia, Jie-Sheng Tian and Teck-Peng Loh. Chem. Rev. 2022, 122, 17479−17646.

Recent Advances in Alkenyl sp2 C−H and C−F Bond Functionalizations: Scope, Mechanism, and Applications


78) Yuan He, Zilong Huang, Kaikai Wu, Juan Ma, Yong-Gui Zhou  and Zhengkun Yu. Chem. Soc. Rev., 202251, 2759.

Recent advances in transition-metal-catalyzed carbene insertion to C–H bonds


79) Isaac F. Yu, Jake W. Wilson, and John F. HartwigChem. Rev. 2023, 10.1021/acs.chemrev.3c00207

Transition-Metal-Catalyzed Silylation and Borylation of C–H Bonds for the Synthesis and Functionalization of Complex Molecules


80) Neil R. Judge, Alessandra Logallo and Eva Hevia.  Chem. Sci., 2023, 10.1039/D3SC03548D.

Main group metal-mediated strategies for C–H and C–F bond activation and functionalisation of fluoroarenes


81) Chen-Xu Liu, Quannan Wang, Qing Gu, and Shu-Li You. Comprehensive Organometallic Chemistry IV . https://doi.org/10.1016/B978-0-12-820206-7.00087-1

C-C Bond Formation Through C-H Activation


82) Saikat Guria, Mirja Md Mahamudul Hassan and Buddhadeb Chattopadhyay. Org. Chem. Front., 2024, doi.org/10.1039/D3QO01931D.

C–H borylation: a tool for molecular diversification


83) Anthony J. Fernandes , Rahul Giri , Kendall N. Houk, and Dmitry Kataye. Angew. Chem. Int. Ed. 2024, e20231837.

Review and Theoretical Analysis of Fluorinated Radicals in Direct CAr H Functionalization of (Hetero)arene


84) Giulia Brufani, Benedetta Di Erasmo, Chao-Jun Li and Luigi Vaccaro. Chem. Sci., 2024, DOI: 10.1039/d4sc00687a.

Csp2 –H functionalization of phenols: an effective access route to valuable materials via Csp2 –C bond formation


85) Jeonghyo Leea and Sukbok Chang. Synlett, 2023, 34, 1356–1366.

Versatile Utility of Cp*Co(III) Catalysts in C–H Amination under Inner- and Outer-Sphere Pathway


86) Gillian McArthur, Jamie H. Docherty, Mishra Deepak Hareram, Marco Simonetti, Iñigo J. Vitorica-Yrezabal, James J. Douglas and Igor Larrosa. Nat. Chem. 2024, DOI: 10.1038/s41557-024-01481-5

An air- and moisture-stable ruthenium precatalyst for diverse reactivity


87) Jidan Liu, Ruilian Liang, Qinglian Yan, Liyao Zheng, Zhao-Qing Liu and Shouzhi Pu. Org. Chem. Front. 2025, DOI: 10.1039/d5qo00111k

Recent advances in the synthesis of nitrogen heterocycles via Rh(III)-catalyzed chelationassisted C–H activation/annulation with diazo compounds


88) Wanle Sheng, Fan Lv, Bing Tang, Erhong Hao, Lijuan Jiao. Chinese Chemical Letters. 2019 , 30, 1825–1833.

Toward the most versatile fluorophore: Direct functionalization of BODIPY dyes via regioselective C–H bond activation



 

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