Ambiphilic Reactivity of Vinyl Pd-Oxyallyl for Expeditious Construction of Highly Functionalized Cyclooctanoids

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.

Automated summary

The catalytic generation of a vinyl Pd-oxyallyl that dimerizes to form highly functionalized nonbridged cyclooctanoids is reported. This compound shows both electrophilic and nucleophilic properties, and the mechanism and origins of chemoselective cyclooctanoid formation are elucidated through DFT calculations.