Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination

We disclose a nickel-catalyzed reaction, which enabled us to difunctionalize unactivated gamma,delta-alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction was made feasible by the use of 5-chloro-8-hydroxyquinoline as a ligand along with NiBr2 center dot DME as a catalyst and LiOtBu as base. The reaction proceeded with a wide range of cyclic, acyclic, endocyclic and exocyclic alkenyl ketones, and electron-rich and electron-deficient arylboronate esters. The reaction also worked with both cyclic and acyclic alkenyl triflates. Control experiments indicate that carbonyl coordination is required for the reaction to proceed.

Automated summary

A nickel-catalyzed reaction was developed for difunctionalizing unactivated gamma,delta-alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction, facilitated by specific ligands and catalysts, demonstrated compatibility with various types of ketones and arylboronate esters, requiring carbonyl coordination for its progress.