A nickel-catalyzed <i>anti</i>-carbometallative cyclization of alkyne–azides with organoboronic acids: synthesis of 2,3-diarylquinolines

Abstract

An anti-carbonickelative cyclization via reversible alkenylnickel E/Z isomerization of 2-azido phenyl propargyl alcohols with aryl boronic acids is achieved using Ni(acac)₂ as the catalyst to access 2,3-diaryl quinolines. It represents a rare example of trapping the vinyl metal intermediate with a nitrogen center, a non-carbon center electrophile.