Nickel/photoredox-catalyzed enantioselective arylation of α-chloro thioesters

Fei Xing; Tingzhi Lin; Yu Ye; Yan-En Wang; Xianzhong Cao; Xueying Gao; Dongzhao Zhang; Lingfeng Kong; Xiyou Zhu; Dan Xiong; Jianyou Mao

doi:10.1039/D3CC04067D

Nickel/photoredox-catalyzed enantioselective arylation of α-chloro thioesters†

Fei Xing,

‡^a Tingzhi Lin,‡^a Yu Ye,^a Yan-En Wang,^b Xianzhong Cao,^a Xueying Gao,^a Dongzhao Zhang,^a Lingfeng Kong,^a Xiyou Zhu,^a Dan Xiong^a and Jianyou Mao

*^a

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* Corresponding authors

^a Technical Institute of Fluorochemistry (TIF), State Key Laboratory of Materials Oriented Chemical Engineering (MCE), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. China
E-mail: ias_jymao@njtech.edu.cn

^b College of Science, Hebei Agricultural University, Baoding 071000, P. R. China

Abstract

The first dual nickel/photoredox-catalyzed enantioselective reductive cross-coupling of racemic α-chloro thioesters with aryl iodides has been developed. This strategy avoids the need for organometallic reagents or stoichiometric metal reductants. This reaction could tolerate a wide range of substrate scope with excellent reactivity and high enantioselectivities (up to 91% ee) to access a variety of chiral α-aryl thioesters. The synthetic utility of the corresponding α-aryl thioesters is demonstrated. Furthermore, we explored the mechanism of such an enantioselective radical cross-coupling process.

Chemical Communications

Nickel/photoredox-catalyzed enantioselective arylation of α-chloro thioesters†

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Nickel/photoredox-catalyzed enantioselective arylation of α-chloro thioesters

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