Ambiphilic Reactivity of Vinyl Pd-Oxyallyl for Expeditious Construction of Highly Functionalized Cyclooctanoids
Linhong Zuo, Pengchen Ma, Teng Liu, Xiangyang Chen, Robert H. Lavroff, Weipeng Chen, K. N. Houk, Wusheng Guo
Abstract
We report the catalytic generation of a vinyl Pd-oxyallyl that dimerizes regiospecifically to form highly functionalized nonbridged cyclooctanoids. Such compounds are otherwise synthetically challenging, but highly useful in synthesis. This vinyl Pd-oxyallyl species demonstrates both electrophilic and nucleophilic properties. DFT calculations elucidate the mechanism and the origins of the chemoselective cyclooctanoid formation.
Topics & Concepts
ChemistryElectrophileReactivity (psychology)NucleophileCatalysisCombinatorial chemistryOrganic chemistryAlternative medicineMedicinePathologyCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms