Photoredox Decarboxylative C(sp³)-N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones

Chun-Ming Chan, Qi Xing, Yip-Chi Chow, Sing-Fung Hung and Wing-Yiu Yu*

*Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, Email: wing-yiu.yupolyu.edu.hk

C.-M. Chan, Q. Xing, Y.-C. Chow, S.-F. Hung, W.-Y. Yu, Org. Lett., 2019, 21, 8037-8043.

DOI: 10.1021/acs.orglett.9b03020

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Abstract

A metal-free photocatalytic coupling reaction of α-diazoacetates and alkyl N-hydroxyphthalimide esters provides structurally and functionally diverse N-alkyl hydrazones. By employing Rose Bengal as a photocatalyst with yellow LEDs irradiation and Hantzsch ester as both an electron donor and proton source, over 60 N-alkyl hydrazones were synthesized.

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Key Words

hydrazones, Hantzsch ester, photochemistry

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ID: J54-Y2019