A new route to sulfonamides via intermolecular radical addition to pentafluorophenyl vinylsulfonate and subsequent aminolysis.
[reaction: see text] Various radical species generated from either the corresponding iodo- or bromo- compounds and tri-n-butyltin hydride were added in an intermolecular fashion to the activated acceptor pentafluorophenyl vinylsulfonate. The products of each reaction were then subjected to aminolysis with a variety of different amines.
Caddick
Stephen
S
Centre for Biomolecular Design and Drug Development, University of Sussex, Falmer, Brighton BN1 9QJ, UK. s.caddick@sussex.ac.uk
Wilden
Jonathan D
JD
Bush
Hannah D
HD
Wadman
Sjoerd N
SN
Judd
Duncan B
DB
D000588:Amines / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D005030:Ethylenes / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis*; D013451:Sulfonic Acids / Q000737:chemistry
D000588:Amines; D005030:Ethylenes; D005609:Free Radicals; D013449:Sulfonamides; D013451:Sulfonic Acids; C085726:ethylenesulfonic acid