Photochemical Doyle–Kirmse Reaction: A Route to Allenes
K Orłowska, Katarzyna Rybicka‐Jasińska, Piotr Krajewski, Dorota Gryko
Abstract
This Letter describes the metal-free, blue-light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yield. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.
Topics & Concepts
ChemistrySulfoniumPropargylYield (engineering)PhotochemistrySinglet stateSigmatropic reactionReactive intermediateMedicinal chemistryOrganic chemistryCatalysisPhysicsExcited stateMetallurgyMaterials scienceSalt (chemistry)Nuclear physicsCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions