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Catalytic sp 3 –sp 3 Functionalisation of Sulfonamides: Late‐Stage Modification of Drug‐Like Molecules
Author(s) -
Abdulla Othman,
Clayton Adam D.,
Faulkner Robert A.,
Gill Duncan M.,
Rice Craig R.,
Walton Scarlett M.,
Sweeney Joseph B.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605464
Subject(s) - catalysis , allylic rearrangement , chemistry , molecule , combinatorial chemistry , chemical synthesis , drug , organic chemistry , medicinal chemistry , stereochemistry , in vitro , psychology , biochemistry , psychiatry
A new application of Pd‐catalysed allylation is reported that enables the synthesis of a range of branched sp 3 ‐functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd 0 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.