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Catalytic sp3–sp3 Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules

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  • Othman Abdulla
  • Adam D. Clayton
  • Robert A. Faulkner
  • Duncan M. Gill
  • Craig R. Rice
  • Scarlett M. Walton
  • Joseph B. Sweeney
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<mark>Journal publication date</mark>31/01/2017
<mark>Journal</mark>Chemistry - A European Journal
Issue number7
Volume23
Number of pages4
Pages (from-to)1494-1497
Publication statusPublished
Early online date18/01/17
Original languageEnglish

Abstract

A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp3-functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd0 catalysts and base at room temperature, direct allylation was efficiently performed, yielding products that are analogues of structural motifs seen in biologically active small molecules. The reaction was performed under mild conditions and could be applied to nanomolar sigma-receptor binders, thus enabling a late-stage functionalisation and efficient expansion of drug-like chemical space.