Isocyanides as Acceptor Groups in MHAT Reactions with Unactivated Alkenes
Jordi Puig, Josep Bonjoch, Ben Bradshaw
Abstract
The use of isocyanides as acceptor groups in metal-hydride hydrogen atom transfer (MHAT) coupling reactions with nonactivated alkenes to form heterocycles is described. Monosubstituted alkenes couple and cyclize directly, whereas more substituted alkenes proceed via a two-step, one-pot procedure involving MHAT reductive cyclization followed by a MHAT Minisci coupling upon the addition of acid. To highlight the utility of the methodology, a diverse variety of substituted heterocycles such as phenanthridines, indoles, and isoquinolines were prepared.
Topics & Concepts
ChemistryHydrideAcceptorHydrogen atomCombinatorial chemistryHydrogenCoupling reactionTransfer hydrogenationOrganic chemistryGroup (periodic table)CatalysisRutheniumPhysicsCondensed matter physicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions