Logeswaran Ravichandran, Jeganmohan Masilamani
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036 Tamil Nadu, India.
Org Lett. 2021 Aug 6;23(15):5679-5683. doi: 10.1021/acs.orglett.1c01797. Epub 2021 Jul 15.
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.
