Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction

A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been established. This method enables the synthesis of 3,5-vicinal carbocyclic rings found in numerous biologically active compounds and natural products. We provide mechanistic experiments that indicate this reaction proceeds through alkyl iodides formed in situ, initiates at the secondary electrophilic center, and proceeds through radical intermediates.

Automated summary

A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been developed for the synthesis of 3,5-vicinal carbocyclic rings found in various biologically active compounds and natural products. Mechanistic experiments suggest that the reaction proceeds through alkyl iodides formed in situ, initiates at the secondary electrophilic center, and proceeds via radical intermediates.