Arylation and alkenylation of activated alkyl halides using sulfonamides

A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S N 2/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. A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S N 2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds.