The aryne Sommelet-Hauser rearrangement

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. © The Royal Society of Chemistry