Just Accepted

This article has been peer reviewed and accepted for publication. It is in production and has not been edited, so may differ from the final published form.

The electrophilic cyanation of alkynyl halides (bromides or chlorides) with N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) via a zinc reagent

Yan Chen, Xiaotong Zhang, Xiao Yun Chen , Cuifeng Yang

Abstract

A novel Zn-mediated preparation of propiolonitrile via electrophilic cyanation of alkynyl bromides with N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) has been achieved here. The zinc dust was firstly used to activate the Csp-Br bond in the presence of tetrabutylammonium iodide (TBAI) to form an alkynyl zinc reagent in situ, which would undergo a nucleophilic addition with NCTS on cyano group to afford an Imine final propiolonitrile after a elimination of Zinc complex. According to this new protocol, Virious phenylpropiolonitriles have been prepared here in moderate to excellent yields (51-95%) form alkynyl bromides, and also could generate from the combination of inactive alkynyl chlorides with tetrabutylammonium bromide (TBAB) in lower yields (20-70%).

CH24055  Accepted 19 March 2025

© CSIRO 2025