Citation: 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. doi: 10.6023/cjoc202004041 shu

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

Corresponding author: Su Weiping, wpsu@fjirsm.ac.cn Kang Qiang, kangq@fjirsm.ac.cn
Received Date: 25 April 2020
Revised Date: 14 May 2020
Available Online: 19 May 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21871261)the National Natural Science Foundation of China 21871261

Figures(3)

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