Catalytic sp 3 -sp 3 Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules

A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp -functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd catalysts and base at room te...

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Bibliographic Details
Published inChemistry : a European journal Vol. 23; no. 7; pp. 1494 - 1497
Main Authors Abdulla, Othman, Clayton, Adam D, Faulkner, Robert A, Gill, Duncan M, Rice, Craig R, Walton, Scarlett M, Sweeney, Joseph B
Format Journal Article
LanguageEnglish
Published Germany 31.01.2017
Subjects
Acetates - chemistry
Allyl Compounds - chemistry
Catalysis
Palladium
Quantum Theory
Sulfonamides - chemistry
Temperature
catalysis
palladium
sulfonamides
late-stage functionalisation
sigma receptor
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Summary:A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp -functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd 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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201605464