Electrochemical C-H Sulfonation of Aminoquinones with Sulfonyl Hydrazides
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Updated: Jun 21, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry, Nanjing University, Nanjing 210023, Jiangsu, China.
Abstract:
We report an efficient, metal-free electrochemical synthesis of sulfonylated aminoquinones via electrooxidative denitrogenation of sulfonyl hydrazides. Anodic denitrogenation generates sulfonyl radicals that undergo chemo- and regioselective addition to aminoquinones, affording diverse products in 52-90% isolated yields with broad functional group tolerance. Mechanistic studies involving cyclic voltammetry and radical trapping support a sulfonyl radical addition pathway. The synthetic utility is demonstrated by converting ortho-fluorophenylsulfonylated products into tetracyclic quinones via base-promoted nucleophilic aromatic substitution.
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