C2-ketonylation of carbohydrates <i>via</i> excited-state palladium-catalyzed 1,2-spin-center shift
Gaoyuan Zhao, Upasana Mukherjee, Ling Zhou, Yue Wu, Wang Yao, Jaclyn N. Mauro, Peng Liu, Ming‐Yu Ngai
Abstract
an excited-state palladium-catalyzed 1,2-spin-center shift (SCS) process. This step-economic reaction features broad substrate scope, has a high functional group tolerance, and can be used in late-stage functionalization of natural product- and drug-glycoconjugates. Preliminary experimental and computational mechanistic studies suggested a non-chain radical mechanism involving photoexcited palladium species, a 1,2-SCS process, and a radical Mizoroki-Heck reaction.
Topics & Concepts
PalladiumChemistryEnolCombinatorial chemistryFunctional groupCatalysisGlycoconjugateExcited stateOrganometallic chemistryOrganic chemistryPolymerPhysicsNuclear physicsBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry