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

Authors :
Abdulla O
Clayton AD
Faulkner RA
Gill DM
Rice CR
Walton SM
Sweeney JB
Source :
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2017 Jan 31; Vol. 23 (7), pp. 1494-1497. Date of Electronic Publication: 2017 Jan 18.
Publication Year :
2017

Abstract

A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp <superscript>3</superscript> -functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd <superscript>0</superscript> 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.<br /> (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1521-3765
Volume :
23
Issue :
7
Database :
MEDLINE
Journal :
Chemistry (Weinheim an der Bergstrasse, Germany)
Publication Type :
Academic Journal
Accession number :
27897342
Full Text :
https://doi.org/10.1002/chem.201605464