Chiral Ligands for Palladium-Catalyzed Coordination-Assisted Enantioselective C(sp3)-H Functionalization Reactions

被引:0
作者
Yuan, Chen-Hui [1 ]
Jiao, Lei [1 ]
机构
[1] Tsinghua Univ, Ctr Basic Mol Sci CBMS, Dept Chem, Beijing 100084, Peoples R China
基金
中国国家自然科学基金;
关键词
palladium catalysis; C(sp(3))-H functionalization; chiral ligands; enantioselectivity; C-H ARYLATION; ALIPHATIC-AMINES; ACTIVATION; BONDS; C(SP(2))-H; ACIDS;
D O I
10.6023/cjoc202406002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective C(sp(3))-H functionalization reactions have emerged as a powerful and straightforward strategy in the construction of chiral molecules. Palladium, highlighted by its remarkable reactivity, versatility, and functional group tolerance, stands out among transition metal catalysts and is one of the most prevalently employed in enantioselective C(sp(3))-H functionalization reactions. In these reactions, chiral ligands play a pivotal role, serving as a decisive factor in controlling both reactivity and stereoselectivity. Focusing on chiral ligands, the latest progress in palladium-catalyzed coordination-assisted enantioselective C(sp(3))-H bond functionalization reactions in recent years is summarized, emphasizing the design concept, reaction mechanism, and stereocontrol model of chiral ligands.
引用
收藏
页码:602 / 619
页数:18
相关论文
共 65 条
[1]   Transition Metal Catalyzed Enantioselective C(sp2)-H Bond Functionalization [J].
Achar, Tapas Kumar ;
Maiti, Sudip ;
Jana, Sadhan ;
Maiti, Debabrata .
ACS CATALYSIS, 2020, 10 (23) :13748-13793
[2]   Enantio- and Diastereoswitchable C-H Arylation of Methylene Groups in Cycloalkanes [J].
Andrae, Michal S. ;
Schifferer, Lukas ;
Pollok, Corina H. ;
Merten, Christian ;
Goossen, Lukas J. ;
Yu, Jin-Quan .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (36) :8503-8507
[3]   Ring Construction by Palladium(0)-Catalyzed C(sp3)-H Activation [J].
Baudoin, Olivier .
ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (04) :1114-1123
[4]   Computational Exploration of a Pd(II)-Catalyzed γ-C-H Arylation Where Stereoselectivity Arises from Attractive Aryl-Aryl Interactions [J].
Bay, Katherine L. ;
Yang, Yun-Fang ;
Houk, K. N. .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (23) :14786-14790
[5]   Palladium(II)-Catalyzed Highly Enantioselective C-H Arylation of Cyclopropylmethylamines [J].
Chan, Kelvin S. L. ;
Fu, Hai-Yan ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (05) :2042-2046
[6]   Ligand-accelerated enantioselective methylene C(sp3)-H bond activation [J].
Chen, Gang ;
Gong, Wei ;
Zhuang, Zhe ;
Andra, Michal S. ;
Chen, Yan-Qiao ;
Hong, Xin ;
Yang, Yun-Fang ;
Liu, Tao ;
Houk, K. N. ;
Yu, Jin-Quan .
SCIENCE, 2016, 353 (6303) :1023-1027
[7]   Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines [J].
Connon, Stephen J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3909-3912
[8]   Pd(II)-Catalyzed Tandem Enantioselective Methylene C(sp3)-H Alkenylation-Aza-Wacker Cyclization to Access β-Stereogenic γ-Lactams [J].
Ding, Yi ;
Han, Ye-Qiang ;
Wu, Le-Song ;
Zhou, Tao ;
Yao, Qi-Jun ;
Feng, Ya-Lan ;
Li, Ya ;
Kong, Ke-Xin ;
Shi, Bing-Feng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (33) :14060-14064
[9]   Late-stage C-H functionalization offers new opportunities in drug discovery [J].
Guillemard, Lucas ;
Kaplaneris, Nikolaos ;
Ackermann, Lutz ;
Johansson, Magnus J. .
NATURE REVIEWS CHEMISTRY, 2021, 5 (08) :522-545
[10]   Pd(II)-Catalyzed Enantioselective Intramolecular Arylation of Unbiased C(sp3)-H Bonds to Construct Chiral Benzo-ring Compounds [J].
Han, Ye-Qiang ;
Zhang, Qi ;
Yang, Xu ;
Jiang, Meng-Xue ;
Ding, Yi ;
Shi, Bing-Feng .
ORGANIC LETTERS, 2021, 23 (01) :97-101