CC BY 4.0 · SynOpen 2023; 07(04): 535-547
DOI: 10.1055/s-0042-1751510
paper
Virtual Collection Electrochemical Organic Synthesis

Oxidative C–H Sulfonylation of Hydrazones Enabled by Electrochemistry

Qi-Liang Yang  ∗
,
Ping-Ping Lei‡
,
Er-Jun Hao
,
Bei-Ning Zhang
,
Hong-Hao Zhou
,
Wan-Wan Li
,
Hai-Ming Guo∗
We are grateful for financial support from the National Natural Science Foundation of China (22007028, U22A20378, and 22071046), the Natural Science Foundation of Henan Province (232300421126), and the Henan Normal University Initiation Fund (5101039170920). The authors also thank the Henan Key Laboratory of Organic Functional Molecules and Drug Innovation for financial support.
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Abstract

An efficient electrochemical oxidative C(sp2)–H sulfonylation of aldehyde hydrazones is described. A variety of sodium sufinates or sulfinic acids participate effectively in this protocol, which provides facile access to an array of alkyl and aromatic sulfonylated hydrazones with up to 96% yield. Large-scale synthesis and product derivatization show the potential utility of this methodology. Preliminary mechanistic investigations including radical-inhibition, electricity on/off experiments, and cyclic voltammetry support a radical pathway.

Key words

electrochemical synthesis - radical - sulfonylation - hydrazones - sulfinic acid

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751510.
  • Supporting Information


Publication History

Received: 04 August 2023

Accepted after revision: 15 September 2023

Article published online:
25 October 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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