SCpRh(III)-Catalyzed Enantioselective Synthesis of Atropisomers by C2-Arylation of Indoles with 1-Diazonaphthoquinones

Si-Yong Yin; Chongqing Pan; Wen-Wen Zhang; Chen-Xu Liu; Fangnuo Zhao; Qing Gu; Shu-Li You

doi:10.1021/acs.orglett.2c01141

SCpRh(III)-Catalyzed Enantioselective Synthesis of Atropisomers by C2-Arylation of Indoles with 1-Diazonaphthoquinones

Org Lett. 2022 May 27;24(20):3620-3625. doi: 10.1021/acs.orglett.2c01141. Epub 2022 May 16.

Authors

Si-Yong Yin¹, Chongqing Pan¹, Wen-Wen Zhang¹, Chen-Xu Liu¹, Fangnuo Zhao¹, Qing Gu¹, Shu-Li You¹

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

PMID: 35575309
DOI: 10.1021/acs.orglett.2c01141

Abstract

The Rh(III)-catalyzed highly enantioselective C2-arylation of indole derivatives with 1-diazonaphthoquinones is reported. In the presence of 2.5 mol % SCpRh complex and 20 mol % AgNO₃, the C2-arylation reactions of indoles proceeded smoothly, affording a wide range of C2-arylated indole atropisomers in good yields and enantioselectivity (≤96% yield, ≤97% ee) under mild conditions. The method displays a broad substrate scope and good functional group tolerance.