A new strategy for the synthesis of benzylic sulfonamides: palladium-catalyzed arylation and sulfonamide metathesis.
An efficient two-step strategy has been developed to access diversely functionalized benzylic sulfonamides. Execution of this strategy required the development of two reaction methods: the palladium-catalyzed cross-coupling of aryl halides with CH-acidic methanesulfonamides and a metathesis reaction between the resulting alpha-arylated sulfonamides and diverse amines. The broad scope of the cross-coupling process combined with a versatile sulfonamide metathesis constitutes an efficient strategy for the synthesis of various benzylic sulfonamides.
Grimm
Jonathan B
JB
Department of Drug Design and Optimization, Merck Research Laboratories, Boston, Massachusetts 02115, USA.
Katcher
Matthew H
MH
Witter
David J
DJ
Northrup
Alan B
AB
D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
D001593:Benzyl Compounds; D013449:Sulfonamides; C036871:methanesulfonamide; D010165:Palladium