The aryne Sommelet-Hauser rearrangement

Chem Commun (Camb). 2019 Mar 5;55(20):3004-3007. doi: 10.1039/c9cc00629j.

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.