Arylation and alkenylation of activated alkyl halides using sulfonamides

Abstract

A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S_N2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C–N and C–C_aryl bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.