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. 2020 Mar 12;56(21):3222-3224.
doi: 10.1039/d0cc00220h.

Arylation and alkenylation of activated alkyl halides using sulfonamides

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Arylation and alkenylation of activated alkyl halides using sulfonamides

Stuart Johnson et al. Chem Commun (Camb). .

Abstract

A variety of quaternary aryl amino acid derivatives can be synthesised using tandem SN2/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-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.

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