Nickel-Catalyzed Three-Component Tandem Radical Cyclization 1,5-Difunctionalization of 1,3-Enynes and Alkyl Bromide

A nickel-catalyzed three-component tandem radical cyclization reaction of aryl bromides with 1,3-enynes and aryl boric acids to construct gamma-lactam-substituted allene derivatives has been described. This protocol provides lactam alkyl radicals through the free radical cyclization process, which can be effectively used to participate in the subsequent multicomponent coupling reaction so that 1,3-enynes could directly convert into corresponding poly substituted allene compounds. In addition, this efficient method enjoys a broad substrate scope and provides a series of 1,5difunctionalized allenes in a one-pot reaction.

Automated summary

A nickel-catalyzed three-component tandem radical cyclization reaction was developed to synthesize gamma-lactam-substituted allene derivatives from aryl bromides, 1,3-enynes, and aryl boric acids. This strategy allowed the lactam alkyl radicals generated through the cyclization process to participate in multicomponent coupling, leading to the direct conversion of 1,3-enynes into poly substituted allene compounds. The method demonstrated wide substrate scope and provided a series of 1,5-difunctionalized allenes in a one-pot reaction.