CC BY 4.0 · SynOpen 2023; 07(04): 535-547
paper
Virtual Collection Electrochemical Organic Synthesis
Oxidative C–H Sulfonylation of Hydrazones Enabled by Electrochemistry
,
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.
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
Publikationsverlauf
Eingereicht: 04. August 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/)
Georg Thieme Verlag KG
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