Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp<sup>2</sup>)–H Alkynylation of Acceptor-Substituted Enamines
Chunyu Han, Xianhai Tian, Huili Zhang, Frank Röminger, A. Stephen K. Hashmi
Abstract
A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp2)–H functionalization of alkenes, offering 26 enynes in 62–92% yield with excellent functional group tolerance.
Topics & Concepts
Hypervalent moleculeChemistryCatalysisYield (engineering)ReagentIodineCombinatorial chemistryAlkynylationFunctional groupAcceptorMedicinal chemistryOrganic chemistryMaterials scienceMetallurgyCondensed matter physicsPhysicsPolymerCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsCatalytic Alkyne Reactions