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

被引：45

作者：

Chan, Chun-Ming ^{[1
]}

Xing, Qi ^{[1
]}

Chow, Yip-Chi ^{[1
]}

Hung, Sing-Fung ^{[1
]}

Yu, Wing-Yiu ^{[1
]}

机构：

[1] Hong Kong Polytech Univ, State Key Lab Chem Biol & Drug Discovery, Dept Appl Biol & Chem Technol, Hung Hom,Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 19期

关键词：

REDOX-ACTIVE ESTERS; DIAZO-COMPOUNDS; BIOLOGICAL-ACTIVITIES; VERSATILE SYNTHONS; ELECTRON-TRANSFER; 1,2,4-TRIAZOLES; N; N-DIALKYLHYDRAZONES; EQUIVALENTS; DIAZOESTERS;

D O I：

10.1021/acs.orglett.9b03020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report a metal-free photocatalytic coupling reaction for the synthesis of structurally and functionally diverse N-alkyl hydrazones from alpha-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(sp(3))-rich N-alkyl hydrazones.

引用

页码：8037 / 8043

页数：7

共 83 条

[81] Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement [J].