Visible-light-induced sulfonylation of Baylis-Hillman acetates under metal- and oxidant-free conditions

A metal-free and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under the irradiation of visible light and open-air conditions at room temperature is described. This transformation has high yields (up to 92%), excellent stereoselectivity, broad subst...

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Veröffentlicht in:New journal of chemistry 2021-12, Vol.45 (47), p.22243-22248
Hauptverfasser: Yang, Cai-Yun, Zhang, De-Run, Hu, Lin-Ping, Li, Xia, Yang, Shi-Chen, Liu, Bo, Huang, Guo-Li
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Sprache:eng
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Zusammenfassung:A metal-free and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under the irradiation of visible light and open-air conditions at room temperature is described. This transformation has high yields (up to 92%), excellent stereoselectivity, broad substrate scope, good functional group tolerance, and mild reaction conditions. Moreover, mechanistic studies indicate that a sulfonyl radical pathway is involved in this reaction. A visible-light-driven metal- and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under open-air conditions at room temperature is reported. The methods provide a green and facile synthetic route to access allylic sulfones.
ISSN:1144-0546
1369-9261
DOI:10.1039/d1nj04878c