Copper-catalyzed amidation of allylic and benzylic C-H bonds.
[Structure: see text] A copper-catalyzed amidation of allylic and benzylic C-H bonds with both primary and secondary sulfonamides is described. The reaction is applicable to the coupling of a diverse set of hydrocarbon species with aryl, heteroaryl, and alkyl sulfonamides and is tolerant of a variety of functional groups. Mechanistic insight has been gained through the isolation of a benzylic acetate intermediate, which was demonstrated to undergo facile conversion to the substituted sulfonamide product under copper catalysis.
Pelletier
Guillaume
G
Merck Frosst Centre for Therapeutic Research, 16711 Trans Canada Highway, Kirkland, Québec H9H 3L1, Canada.
Powell
David A
DA
D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*
D000577:Amides; D003300:Copper