Benzylic C(sp³)-H Bonds Play the Dual Role of Starting Material and Oxidation Inhibitor for Hydrazides in the Electrochemical Synthesis of Hydrazones

Issa Yavari* and Sina Shaabanzadeh

*Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran 1463694571, Iran, Email: yavarisamodares.ac.ir

I. Yavari, S. Shaabanzadeh, J. Org. Chem., 2022, 87, 15077-15085.

DOI: 10.1021/acs.joc.2c01574

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Abstract

An electrooxidation of benzylic C(sp³)-H bonds to produce hydrazones avoids the use of hazardous metal catalysts and external oxidants in aqueous media in the presence of NaCl as cheap electrolyte. This strategy provides hydrazones with various functional groups in good efficiency while the highly oxidizable hydrazide group remains intact. The reaction is suitable for gram-scale synthesis.

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proposed mechanism

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Key Words

hydrazones, electrochemistry

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ID: J42-Y2022