Pd(II)-Catalyzed C═C Bond Cleavage by a Formal Group-Exchange Reaction
Runyou Ye, Maoshuai Zhu, Xufei Yan, Yang Long, Ying Xia, Xiangge Zhou
Abstract
A chelation-assisted palladium-catalyzed C═C bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1═C2 + C3 → C1═C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.
Topics & Concepts
NitrileChemistryAlkeneCatalysisMetathesisCleavage (geology)PalladiumBond cleavageKetoneMedicinal chemistryChelationOxidative additionStereochemistryOrganic chemistryPolymerEngineeringGeotechnical engineeringFracture (geology)PolymerizationCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry MethodsCatalytic Cross-Coupling Reactions