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Direct synthesis of hydrazones by visible light mediated aerobic oxidative cleavage of the CC bond†
Ya Ding,Hao Li,Yunge Meng,Te Zhang,Jiawen Li,Qiu-Yun Chen
Organic Chemistry Frontiers Pub Date : 05/15/2017 00:00:00 , DOI:10.1039/C7QO00276A
Abstract

A metal-free protocol through visible light mediated oxidative cleavage of C[double bond, length as m-dash]C bonds to directly construct C[double bond, length as m-dash]N bonds has been developed for the conversion of alkenes to hydrazones under mild conditions. The reaction involves a diazetidine intermediate that is generated by [2 + 2] annulation of alkenes with diazenes generated in situ by single-electron oxidation of arylhydrazines. The key features of this reaction include a broad substrate scope and readily available reagents.

Graphical abstract: Direct synthesis of hydrazones by visible light mediated aerobic oxidative cleavage of the C [[double bond, length as m-dash]] C bond
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