Palladium-Catalyzed Synthesis of Functionalized Indoles by Acylation/Allylation of 2-Alkynylanilines with Three-Membered Rings
Weiliang Yuan, Xiaojiao Li, Xiaojiao Li, Zisong Qi, Xingwei Li, Xingwei Li
Abstract
Palladium-catalyzed synthesis of 3-acyl and -allyl indoles has been realized by merging nucleophilic cyclization of ortho-alkynylanilines with ring opening of three-membered rings such as cyclopropenones and gem-difluorinated cyclopropanes. These functionalized indoles were obtained in moderate to high yields with high stereoselectivity in both cases. This protocol provides an alternative method toward functionalized indoles under mild and redox-neutral conditions.
Topics & Concepts
ChemistryAcylationNucleophileCatalysisPalladiumRing (chemistry)StereoselectivityCombinatorial chemistryOrganic chemistryMedicinal chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Alkyne Reactions