Visible-Light-Induced Decarboxylative Cyclization of 2-Alkenylarylisocyanides with α-Oxocarboxylic Acids: Access to 2-Acylindoles

Xiaofei Zhang; Peiyuan Zhu; Ruihong Zhang; Xiang Li; Tuanli Yao

doi:10.1021/acs.joc.0c00039

Visible-Light-Induced Decarboxylative Cyclization of 2-Alkenylarylisocyanides with α-Oxocarboxylic Acids: Access to 2-Acylindoles

J Org Chem. 2020 Aug 7;85(15):9503-9513. doi: 10.1021/acs.joc.0c00039. Epub 2020 Jul 9.

Authors

Xiaofei Zhang^{1

2}, Peiyuan Zhu¹, Ruihong Zhang¹, Xiang Li^{1

2}, Tuanli Yao^{1

2}

Affiliations

¹ College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an, Shaanxi 710021, China.
² Shaanxi Key Laboratory of Chemical Additives for Industry, Shaanxi University of Science and Technology, Xi'an 710021, China.

PMID: 32600039
DOI: 10.1021/acs.joc.0c00039

Abstract

An efficient and practical protocol for visible-light-induced decarboxylative cyclization of 2-alkenylarylisocyanides with α-oxocarboxylic acids has been developed, which afforded a broad range of 2-acylindoles in moderate to good yields. The reaction proceeds through a cascade of acyl radical addition/cyclization reactions under irradiation of an Ir³⁺ photoredox catalyst without external oxidants and features simple operation, scalability, a broad substrate scope, and good functional group tolerance.