Copper-Catalyzed Intramolecular Olefinic C(sp²)–H Amidation for the Synthesis of <i>γ</i>-Alkylidene-<i>γ</i>-lactams

Abstract

Herein, we report the copper-catalyzed dehydrogenative C(sp2)–N bond formation of 4-pentenamides via nitrogen-centered radicals. This reaction provides a straightforward and efficient preparation method for γ-alkylidene-γ-lactams. Notably, we could controllably synthesize α,β-unsaturated- or α,β-saturated-γ-alkylidene-γ-lactams depending on the reaction conditions.

Keywords

• C(sp²)–H amidation
• <i>γ</i>-alkylidene-<i>γ</i>-lactam
• nitrogen-centered radical
• cross-dehydrogenative coupling
• copper-catalyst