The aryne Sommelet–Hauser rearrangement

Abstract

An aryne induced transition-metal-free and mild Sommelet–Hauser rearrangement of tertiary benzylamines for the synthesis of α-aryl amino acid derivatives in moderate to good yields is presented. Unlike the conventional Sommelet–Hauser rearrangement of ammonium salts, the methodology developed herein requires neither harsh conditions nor strong bases. Moreover, a temperature dependent switchable selectivity for the Sommelet–Hauser and Stevens [1,2] rearrangements has been observed.