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.