Me3SiBr-promoted cascade electrophilic thiocyanation/cyclization of ortho-alkynylanilines to synthesize indole derivatives

Qing Wang; Chukai Shao; Ruirui Hua; Hongquan Yin; Fu-Xue Chen

doi:10.1039/d4ob00367e

Me₃SiBr-promoted cascade electrophilic thiocyanation/cyclization of ortho-alkynylanilines to synthesize indole derivatives

Org Biomol Chem. 2024 May 1. doi: 10.1039/d4ob00367e. Online ahead of print.

Authors

Qing Wang¹, Chukai Shao¹, Ruirui Hua¹, Hongquan Yin^{1

2}, Fu-Xue Chen^{1

2}

Affiliations

¹ School of Chemistry & Chemical Engineering, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China. fuxue.chen@bit.edu.cn.
² Key Laboratory of Medical Molecule Science and Pharmaceutics Engineering, Ministry of Industry and Information Technology, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China.

PMID: 38690868
DOI: 10.1039/d4ob00367e

Abstract

A Lewis acid-promoted electrophilic thiocyanation/cyclization of ortho-alkynylanilines for the synthesis of indole derivatives has been developed. The reaction utilizes Me₃SiBr as the Lewis acid and N-thiocyanatosuccinimide as the thiocyanation reagent. A series of 2-aryl-3-thiocyanato indoles were prepared in moderate to high yields under mild conditions without metals and oxidants. It provides an efficient protocol for the construction of the indole skeleton and C-SCN and C-N bonds in one step as well.