Furan Synthesis via Triplet Sensitization of Acceptor/Acceptor Diazoalkanes
Siqi Zhu, Fang Li, Claire Empel, Sripati Jana, Chao Pei, René M. Koenigs
Abstract
Abstract Herein, we report on the photocatalytic reaction of acceptor/acceptor diazoalkanes with terminal alkynes. Experimental and computational studies suggest the formation of a key triplet carbene intermediate that undergoes an addition reaction to the alkyne followed by cyclization to give furan heterocycles (31 to 90% yield). This reaction was studied with a broad range of alkynes and acceptor/acceptor diazoalkanes and now provides access to furans under mild reaction conditions. magnified image
Topics & Concepts
ChemistryAcceptorFuranCarbenePhotochemistryAlkyneYield (engineering)CatalysisOrganic chemistryMetallurgyPhysicsCondensed matter physicsMaterials scienceCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions