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Photoredox-catalyzed sulfonylation of alkenylcyclobutanols with the insertion of sulfur dioxide through semipinacol rearrangement

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Abstract

A photoredox-catalyzed sulfonylation of alkenylcyclobutanols with the insertion of sulfur dioxide through semipinacol rearrangement under visible light irradiation is developed. This protocol provides an efficient and facile route to β-sulfonated ketones bearing α-carbon quaternary centers under mild conditions, which features good functional group compatibility. Preliminary mechanistic investigation shows that an arylsulfonyl radical-induced 1,2-carbon migration process is involved.

Graphical abstract: Photoredox-catalyzed sulfonylation of alkenylcyclobutanols with the insertion of sulfur dioxide through semipinacol rearrangement

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Publication details

The article was received on 26 Feb 2019, accepted on 04 Apr 2019 and first published on 11 Apr 2019


Article type: Research Article
DOI: 10.1039/C9QO00300B
Citation: Org. Chem. Front., 2019, Advance Article

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    Photoredox-catalyzed sulfonylation of alkenylcyclobutanols with the insertion of sulfur dioxide through semipinacol rearrangement

    F. He, Y. Wu, X. Li, H. Xia and J. Wu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00300B

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