Arylation and Alkenylation of Activated Alkyl Halides using Sulfonamides

A variety of quaternary aryl amino acid derivatives can be synthesised using tandem SN2 / Smiles rearrangement chemistry involving aryl sulfonamides and alpha-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-Caryl 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