Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex

doi:10.6023/cjoc202004041

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3944-3952.DOI: 10.6023/cjoc202004041 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑；创刊四十周年专辑

中心手性金属铑配合物催化的不对称光诱导Giese自由基加成反应

陈亮^a,b, 胡良建^a,c, 杜宇^a, 苏伟平^a, 康强^a

a 中国科学院福建物质结构研究所结构化学国家重点实验室福州 350002;
b 中国科学院大学北京 100049;
c 福建农林大学材料工程学院福州 350002

收稿日期:2020-04-25 修回日期:2020-05-14 发布日期:2020-05-20
通讯作者: 苏伟平, 康强 E-mail:wpsu@fjirsm.ac.cn,kangq@fjirsm.ac.cn
基金资助:
国家自然科学基金面上（No.21871261）资助项目.

Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex

Chen Liang^a,b, Hu Liangjian^a,c, Du Yu^a, Su Weiping^a, Kang Qiang^a

a State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002;
b University of Chinese Academy of Sciences, Beijing 100049;
c College of Material Engineering, Fujian Agriculture and Forestry University, Fuzhou 350002

Received:2020-04-25 Revised:2020-05-14 Published:2020-05-20
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21871261).

1. cjoc202004041辅助材料.pdf(2070KB)

Abstract

A visible-light driven asymmetric Giese radical addition catalyzed by a bifunctional chiral-at-metal rhodium complex has been developed. para-Aminobenzyl radicals generated from para-aminophenylacetic acids could undergo a 1,4-addition in a highly enantioselective approach to α,β-unsaturated 2-acyl imidazoles, and a variety of corresponding adducts were obtained in moderate to high yields with excellent enantioselectivities. This reaction features high enantioselectivity, mild reaction conditions and an operationally simple procedure. A plausible reaction mechanism is proposed based on our research and literature precedents on dual functional chiral-at-metal catalysis.

Key words: visible-light photoredox catalysis, bifunctional chiral-at-metal rhodium complex, Giese radical addition, para-aminobenzyl radical

Cite this article

Chen Liang, Hu Liangjian, Du Yu, Su Weiping, Kang Qiang. Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3944-3952.

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中心手性金属铑配合物催化的不对称光诱导Giese自由基加成反应

Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex

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