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Arylation and Alkenylation of Activated Alkyl Halides using Sulfonamides

Abstract

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

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Article information


Submitted
09 Jan 2020
Accepted
11 Feb 2020
First published
14 Feb 2020

Chem. Commun., 2020, Accepted Manuscript
Article type
Communication

Arylation and Alkenylation of Activated Alkyl Halides using Sulfonamides

M. Greaney, S. Johnson and E. Kovács, Chem. Commun., 2020, Accepted Manuscript , DOI: 10.1039/D0CC00220H

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