A Counterion/Ligand-Tuned Chemo- and Enantioselective Copper- Catalyzed Intermolecular Radical 1,2-Carboamination of Alkenes

Cheng, Xian-Yan1; Zhang, Yu-Feng1; Wang, Jia-Huan1; Gu, Qiang-Shuai2; Li, Zhong-Liang2; Liu, Xin-Yuan1

2022-09-01

10.1021/jacs.2c08035

Journal of the American Chemical Society   Impact Factor & Quartile

0002-7863

1520-5126

The copper-catalyzed enantioselective intermolecular radical 1,2-carboamination of alkenes with readily accessible alkyl halides is an appealing strategy for producing chiral amine scaffolds. The challenge arises from the easily occurring atom transfer radical addition between alkyl halides and alkenes and the issue of enantiocontrol. We herein describe a radical alkene 1,2-carboamination with sulfoximines in a highly chemo-and enantioselective manner. The key to the success of this process is the conceptual design of a counterion/highly sterically demanded ligand coeffect to promote the ligand exchange of copper(I) with sulfoximines and forge chiral C-N bonds between alkyl radicals and the chiral copper(II) complex. The reaction covers alkenes bearing distinct electronic properties, such as aryl-, heteroaryl-, carbonyl-, and aminocarbonyl-substituted ones, and various radical precursors, including alkyl chlorides, bromides, iodides, and the CF3 source. Facile transformations deliver many chiral amine building blocks of interest in organic synthesis and related areas.

SCI

English

NI Journal Papers

First ; Corresponding

[2021YFF0701604] ; [2021YFF0701704] ; [22025103] ; [21831002] ; [2019BT02Y335] ; [2020B121201002] ; [2021A1515110093] ; [JCYJ20200109141001789]

Chemistry

Chemistry, Multidisciplinary

WOS:000862116900001

AMER CHEMICAL SOC

Web of Science

1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Dept Chem, Shenzhen 518055, Peoples R China

Cheng, Xian-Yan,Zhang, Yu-Feng,Wang, Jia-Huan,et al. A Counterion/Ligand-Tuned Chemo- and Enantioselective Copper- Catalyzed Intermolecular Radical 1,2-Carboamination of Alkenes[J]. Journal of the American Chemical Society,2022.

Cheng, Xian-Yan,Zhang, Yu-Feng,Wang, Jia-Huan,Gu, Qiang-Shuai,Li, Zhong-Liang,&Liu, Xin-Yuan.(2022).A Counterion/Ligand-Tuned Chemo- and Enantioselective Copper- Catalyzed Intermolecular Radical 1,2-Carboamination of Alkenes.Journal of the American Chemical Society.

Cheng, Xian-Yan,et al."A Counterion/Ligand-Tuned Chemo- and Enantioselective Copper- Catalyzed Intermolecular Radical 1,2-Carboamination of Alkenes".Journal of the American Chemical Society (2022).