Palladium-catalyzed C–H glycosylation and retro Diels–Alder tandem reaction <i>via</i> structurally modified norbornadienes (smNBDs)
Yang An, Bo‐Sheng Zhang, Yanan Ding, Zhe Zhang, Xue‐Ya Gou, Xuesong Li, Xiaolei Wang, Yuke Li, Yong‐Min Liang
Abstract
-alkyl (primary, secondary and tertiary) C4-glycosidic indoles can also be obtained by this method. In terms of mechanism, the key ANP intermediates characterized by X-ray single-crystal diffraction and further controlled experiments proved that the migration-insertion of smNBDs with phenylpalladium intermediate endows them with high chemo- and regioselectivity. Finally, density functional theory (DFT) calculation further verified the rationality of the mechanism.
Topics & Concepts
PalladiumGlycosylationChemistryTandemDiels–Alder reactionCatalysisCombinatorial chemistryOrganic chemistryStereochemistryBiochemistryMaterials scienceComposite materialCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions