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不对称C-H键活化综述

May,29, 2021

不对称C-H键活化综述

 

1) C. G. Newton, S.-G. Wang, C. C. Oliveira, N. Cramer, Chem. Rev. 2017, 117, 8908;

Catalytic Enantioselective Transformations Involving C–H Bond Cleavage by Transition-Metal Complexes


2) D.-W. Gao, Q. Gu, C. Zheng, S.-L. You, Acc. Chem. Res. 2017, 50, 351;

Synthesis of Planar Chiral Ferrocenes via Transition-Metal-Catalyzed Direct C–H Bond Functionalization


3) G. Liao, T. Zhou, Q. J. Yao, B. F. Shi, Chem. Commun. 2019, 55, 8514;

Recent advances in the synthesis of axially chiral biaryls via transition metal-catalysed asymmetric C–H functionalization


4) J. Diesel, N. Cramer, ACS Catal. 2019, 9, 9164;

Generation of Heteroatom Stereocenters by Enantioselective C−H Functionalization


5) T. K. Achar, S. Maiti, S. Jana, D. Maiti, ACS Catal. 2020, 10, 13748;

Transition Metal Catalyzed Enantioselective C(sp2)−H Bond Functionalization


6) M. I. Lapuh, S. Mazeh, T. Besset, ACS Catal. 2020, 10, 12898;

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


7) T. Yoshino, S. Satake, S. Chem. Eur. J. 2020, 26, 7346;

Diverse Approaches for Enantioselective C-H Functionalization Reactions Using Group 9 CpxMIII Catalysts


8) L. Woźniak, J.-F. Tan, Q.-H. Nguyen, A. Madron du Vigné, V. Smal, Y.-X. Cao, N. Cramer, Chem. Rev. 2020, 120, 10516;

Catalytic Enantioselective Functionalizations of C−H Bonds by Chiral Iridium Complexes


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

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


10) J. Mas-Roselló, A. G. Herraiz, B. Audic, A. Laverny, N. Cramer, Angew. Chem. Int. Ed. DOI: 10.1002/anie.202008166;

Chiral Cyclopentadienyl Ligands: Design, Syntheses, and Applications in Asymmetric Catalysis


11) T. Yoshino, S. Matsunaga, ACS Catal. 2021, 11, 6455.

Chiral Carboxylic Acid Assisted Enantioselective C−H Activation with Achiral CpxMIII (M = Co, Rh, Ir) Catalysts


12) Q. Gu, Z.-J. Wu , S.-L. You, Bull. Chem. Soc. Jpn. 2021, 94, 641.

Recent Advances in Enantioselective Direct C-H Addition to Carbonyls and Michael Acceptors


13) C.-X. Liu, W.-W. Zhang, S.-Y. Yin, Q. Gu, and S.-L. You, J. Am. Chem. Soc. 2021, 143, 35, 14025–14040.

Synthesis of Atropisomers by Transition-Metal-Catalyzed Asymmetric C–H Functionalization Reaction


14) Q. Zhang and B.-F. Shi, Acc. Chem. Res. 2021, 54, 12, 2750–2763.

2‑(Pyridin-2-yl)isopropyl (PIP) Amine: An Enabling Directing Group for Divergent and Asymmetric Functionalization of Unactivated Methylene C(sp3 )−H Bonds.


15) Q. Wang, C.-X. Liu, Q. Gu, S.-L. You, Sci. Bull., 2021, 66, 210–213.

Chiral Cpx Rh complexes for C–H functionalization reactions.   


16) Bo Su,John F. Hartwig. DOI : 10.1002/anie.202113343

Development of Chiral Ligands for the Transition Metal-catalyzed Enantioselective Silylation and Borylation of C-H Bonds   


17) Qi Zhang, Le-Song Wu, and Bing-Feng Shi.  Chem 8, 1–30, February 10, 2022

Forging C-heteroatom bonds by transition metal-catalyzed enantioselective C–H functionalization 


18) Jin-Bao Peng, Xin-Lian Liu, Lin Li & Xiao-Feng Wu. DOI:10.1007/s11426-021-1165-6

Palladium-catalyzed enantioselective carbonylation reactions    


19) Joanna Wencel-Delord, Françoise Colobert.  SynOpen 2020, 4, 107–115

Challenging Atroposelective C–H Arylation


20) Bo Su, and John F. Hartwig. Angew. Chem. Int. Ed. 2021, 60, 2–16Angew. Chem. Int. Ed.

2021,60,2–16

Angew. Chem. Int. Ed.

2021,60,2–16

Development of Chiral Ligands for the Transition Metal-catalyzed Enantioselective Silylation and Borylation of C-H Bonds


21) Shenghan Teng and Jianrong Steve Zhou. Chem. Soc. Rev., 2022, 51, 1592–1607Angew. Chem. Int. Ed.

2021,60,2–16

Angew. Chem. Int. Ed.

2021,60,2–16

Metal-catalyzed asymmetric heteroarylation of alkenes: diverse activation mechanisms


22) Xin Yu, Zhuo-Zhuo Zhang,  Jun-Long Niu and Bing-Feng Shi. Org. Chem. Front., 2022, 9, 1458–1484.

Angew. Chem. Int. Ed.

2021,60,2–16

Angew. Chem. Int. Ed.

2021Coordination-assisted, transition-metal-catalyzed enantioselective desymmetric C–H functionalization


23) Mingliang Li and Jun (Joelle) Wang. Synthesis, 2022, 54, 4734–4752.

Recent Advances on Transition-Metal-Catalyzed Asymmetric C–H Arylation Reactions


24) Achim Link and Christof Sparr. Chem. Soc. Rev., 2018, 47, 3804--3815.

Stereoselective arene formation


25) Caitlin Davies, Saad Shaaban and Herbert Waldmann. doi: 10.1016/j.trechm.2022.01.005.

Asymmetric catalysis with chiral cyclopentadienyl complexes to access privileged scaffolds


26) Yang Zheng, Chao Zheng, Qing Gu and Shu-li You. Chem Catalysis, 2022, 2, 2965-2985.

Enantioselective C−H functionalization reactions enabled by cobalt catalysis


27) Qi Zhang, Le-Song Wu and Bing-Feng Shi. Chem, 2022, 8, 384–413.

Forging C-heteroatom bonds by transition-metal-catalyzed enantioselective C–H functionalization


28) Bei-Bei Zhan, Liang Jin and Bing-Feng Shi. Trends in Chemistry, 2022, 4, 220-235.

Palladium-catalyzed enantioselective C–H functionalization via C–H palladation


29) Chen-Xu Liu, Qing Gu and Shu-Li You. Trends in Chemistry, 2020, 2, 737-749.

Asymmetric C–H Bond Functionalization of Ferrocenes: New Opportunities and Challenges


30) Łukasz Wozniak and Nicolai Cramer. Trends in Chemistry, 2019, 1, 471-484.

Enantioselective C–H Bond Functionalizations by 3d Transition-Metal Catalysts


31) Yang H, Gou B B, Dai H T, Gu Q, You S L. Sci Sin Chim, 2023, 53, 359–374.

Advances in the synthesis of chiral cyclopentadienyl ligands and metal complexes


32) Sabine Choppin and Joanna Wencel-Delord. Acc. Chem. Res. 2023, 56, 189−202.

Sulfoxide-Directed or 3d-Metal Catalyzed C−H Activation and Hypervalent Iodines as Tools for Atroposelective Synthesis


33) Xiaohong Chen, Xue Gong, Bo Wang and Guoyong Song. C–H Activation for Asymmetric Synthesis.

Non-stereoselective C(sp2)–H Activation Followed by Selective Functionalization of Metallacyclic Intermediate


34) Xandro Vidal, Marc Font, Moisés Gulías, and José L. Mascareñas. Handbook of CH-Functionalization, © 2023 WILEY-VCH GmbH. DOI:10.1002/9783527834242.chf0138.

Transition Metal-Catalyzed Desymmetrizations Based on C––H Activation Processes


35) Tapas Kumar Achar, Shaeel Ahmed Al-Thabaiti, Mohamed Mokhtar and Debabrata Maiti. Chem Catalysis, 2023, 3, 100575.

Enantioselective annulation reactions through C(sp2 )–H activation with chiral CpxMIII catalysts


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

Dirhodium: carbene transformations and beyond


37) Li Li, Wei-Sheng Huang, Zheng Xu and Li-Wen Xu. Sci China Chem, 2023, 66: 1654–1687.

Catalytic asymmetric silicon-carbon bond-forming transformations based on Si–H functionalization


38) Chen-Xu Liu, Si-Yong Yin, Fangnuo Zhao, Hui Yang, Zuolijun Feng, Qing Gu and Shu-Li You. Chem. Rev. 2023, 123, 10079–10134.

Rhodium-Catalyzed Asymmetric C–H Functionalization Reactions


39) Yichen Wu, Long Zheng, Yan Wang and Peng Wang. Chem. 2023, DOI:10.1016/j.chempr.2023.09.024.

Catalytic asymmetric synthesis of silicon-stereogenic organosilanes    


40) Alexander Fanourakis and Robert J. Phipps. Chem. Sci., 2023, DOI: 10.1039/d3sc04661c.

Catalytic, asymmetric carbon–nitrogen bond formation using metal nitrenoids: from metal–ligand complexes via metalloporphyrins to enzymes


41) Heng-Hui Li, Xuemeng Chen and Søren Kramer. Chem. Sci., 2023, https://doi.org/10.1039/D3SC04643E.

Recent developments for intermolecular enantioselective amination of non-acidic C(sp3 )–H bonds 


42) Pu-Fan Qian, Jun-Yi Li, Yi-Bo Zhou, Tao Zhou and Bing-Feng Shi. SynOpen, 2023, 7, 466–485.

Half-Sandwich d6-Metal (CoIII, RhIII, IrIII, RuII)-Catalyzed Enantioselective C–H Activation


43) Qihang Guo, Xuzhong Shen and Zhan Lu. Chin. J. Chem. 2024, 42, 760-776.

Recent Advances in Enantioselective Reactions of Terminal Unactivated Alkenes


44) Guo-Qiang Xu, Wei David Wang and Peng-Fei Xu. J. Am. Chem. Soc. 2024, 146, 1209–1223.

Photocatalyzed Enantioselective Functionalization of C(sp3)–H Bonds 


45) Bholanath Garai, Abir Das, Doppalapudi Vineet Kumar and Basker Sundararaju. Chem. Commun., 2024, doi.org/10.1039/D3CC05329F

Enantioselective C–H bond functionalization under Co(iii)-catalysis


46) Yue Zhang, Jing-Jing Zhang, Lujun Lou, Ruofan Lin, Nicolai Cramer, Shou-Guo Wang and Zhen Chen. Chem. Soc. Rev., 2024, DOI: 10.1039/D3CS00762F

Recent advances in Rh(I)-catalyzed enantioselective C–H functionalization


47) Zexian Li and Zhuangzhi Shi. Acc. Chem. Res.2024, DOI: 10.1021/acs.accounts.4c00020

Late-Stage Diversification of Phosphines by C−H Activation: A Robust Strategy for Ligand Design and Preparation


48) Mikhail A. Boym, Roman A. Pototskiy, Evgeniya S. Podyacheva, Denis A. Chusov,  Yulia V. Nelyubinaac and Dmitry S. Perekalin. Chem. Commun., 2024, DOI: 10.1039/d4cc00181h

Planar-chiral arene ruthenium complexes: synthesis, separation of enantiomers, and application for catalytic C–H activation


49) Hui Yang, Ru Zhang, Su-Zhen Zhang, Qing Gu and Shu-Li You. ACS Catal. 2023, 13, 8838−8844.

Synthesis of Hexamethyl-1,1′-spirobiindane-Based Chiral Spiro Cp Ligands and Their Application in Rhodium-Catalyzed Enantioselective Aryl C−H Addition to Nitroalkenes


50) Chunhui Zhang, Jijun Jiang, Xiaoyu Huang and Jun Wang. ACS Catal. 2023, 13, 10468−10473.

Planar-Chiral Cyclopentadienyl Rhodium Catalysts: Design Concept, Chiral Resolution Strategy, and Applications


51) Timothy P. Aldhous, Raymond W. M. Chung, Andrew G. Dalling, John F. Bower. Synthesis. 2021, 53, 2961-2965.

Enantioselective Intermolecular Murai-Type Alkene Hydroarylation Reactions


52) Qiang Yue, Bin Liu, Gang Liao and Bing-Feng Shi. ACS Catal. 2022, 12, 9359−9396.

Binaphthyl Scaffold: A Class of Versatile Structure in Asymmetric C−H Functionalization


53) TAKAHIKO AKIYAMA, IWAO OJIMA. (Book)

CATALYTIC ASYMMETRIC SYNTHESIS


54) Zhongyi Zeng, Huiying Xu, Hui Gao, Zhi Zhou, Wei Yi. Coordination Chemistry Reviews. 2025, 522, 216244.

Experimental and computational journey on transition-metal-catalyzedC–H functionalization with fluorinated π-systems


55) Zexian Li and Zhuangzhi Shi. Acc. Chem. Res. 2024, 57, 1057−1072

Late-Stage Diversification of Phosphines by C−H Activation: A Robust Strategy for Ligand Design and Preparation


56) En-Ze Lin and Bi-Jie Li. Chin. J. Org. Chem. 2024, 44. DOI: 10.6023/cjoc202406049

Recent Progress in Metal-Catalyzed Asymmetric Hydroarylation of Internal Alkenes Through C-H Cleavage


57) Bholanath Garai, Abir Das, Doppalapudi Vineet Kumar and Basker Sundararaju. Chem. Commun. 2024, 60, 3354

Enantioselective C–H bond functionalizationunder Co(III)-catalysis


58) Shiyan Cheng, Qianyu Li, Xiuliang Cheng, Yu-Mei Lin and Lei Gong. Chin. J. Chem. 2022, 40, 2825—2837.

Recent Advances in Asymmetric Transformations of Unactivated Alkanes and Cycloalkanes through Direct C—H Functionalization


59) Devesh Chandra, Tammana Sharma, Sarthi, Sachin, Upendra Sharma. Journal of Catalysis. 2024, 439, 115756.

Chiral metal complexes: Design strategies for precision in asymmetric C–H activation


60) Guanlin Li, Xiaohong Huo, Xieyang Jianga and Wanbin Zhang. Chem. Soc. Rev. 202049, 2060.

Asymmetric synthesis of allylic compounds viahydrofunctionalisation and difunctionalisationof dienes, allenes, and alkynes


61) Chong-Lei Ji, Xi-Zhang Zou and De-Wei Gao. Angew. Chem. Int. Ed. 2025, e202504224.

Catalytic Asymmetric Construction of Nonadjacent Stereoelements


62) Qi-Jun Yao and Bing-Feng Shi. Acc. Chem. Res. 2025, 58, 971−990.

Cobalt(III)-Catalyzed Enantioselective C−H Functionalization: Ligand Innovation and Reaction Development


63) Pu-Fan Qian, Jun-Yi Li, Yi-Bo Zhou, Tao Zhou and Bing-Feng Shi. SynOpen. 2023, 7, 466–485.

Half-Sandwich d6-Metal (CoIII, RhIII, IrIII, RuII)-Catalyzed Enantioselective C–H Activation



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