Effect of Transition Metals on Chemodivergent Cross-Coupling of Acrylamides with Vinyl Acetate via C–H Activation
Ravichandran Logeswaran, Masilamani Jeganmohan
Abstract
A novel chemodivergent cross-coupling of acrylamides and vinyl acetates has been realized via metal-catalyzed vinylic C-H activation. The selective olefinic C-H vinylation and alkenylation reaction was examined with a variety of differently functionalized acrylamides. The reaction efficiently generates a range of highly synthetically valuable butadienes with good functional group tolerance in good to moderate yields. A possible catalytic reaction mechanism involving the chelation-assisted olefinic C-H activation via an acetate-assisted deprotonation pathway is proposed.
Topics & Concepts
ChemistryDeprotonationCatalysisChelationTransition metalVinyl acetateFunctional groupCoupling reactionPolymer chemistryCombinatorial chemistryOrganic chemistryMedicinal chemistryCopolymerIonPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling Reactions