Oxidative C–H Sulfonylation of Hydrazones Enabled by Electrochemistry

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%...

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Published inSynOpen (2017) Vol. 7; no. 4; pp. 535 - 547
Main Authors Yang, Qi-Liang, Lei, Ping-Ping, Hao, Er-Jun, Zhang, Bei-Ning, Zhou, Hong-Hao, Li, Wan-Wan, Guo, Hai-Ming
Format Journal Article
LanguageEnglish
Published Georg Thieme Verlag KG 01.10.2023
Subjects
electrochemical synthesis
hydrazones
radical
sulfinic acid
sulfonylation
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Summary: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.
ISSN:2509-9396
2509-9396
DOI:10.1055/s-0042-1751510