Photoredox decarboxylative C(sp³)-N coupling of α-diazoacetates with alkyl N-hydroxyphthalimide esters for diversified synthesis of functionalized N-alkyl hydrazones

Abstract

Herein we report a metal-free photocatalytic coupling reaction for the synthesis of structurally and functionally diverse N-alkyl hydrazones from α-diazoacetates and N-alkyl hydroxyphthalimide esters. By employing Rose Bengal as a photocatalyst with yellow LEDs irradiation, over 60 N-alkyl hydrazones were synthesized. Fluorescence quenching analysis and deuterium incorporation experiments reveal that Hantzsch ester serves as both an electron donor and proton source for the reaction. This strategy offers a simple retrosynthetic disconnection for conventionally inaccessible C(sp³)-rich N-alkyl hydrazones.