Issue 16, 2018

Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide under photocatalysis

Abstract

Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide promoted by visible light is developed. The combination of 4-substituted pent-4-en-1-ols, DABCO·(SO2)2, and aryldiazonium tetrafluoroborates under mild conditions in the presence of a photocatalyst provides sulfonated 2,2-disubstituted tetrahydrofurans in moderate to good yields. Moreover, this protocol can be further extended to 5-phenylhex-5-en-1-ol and [2-(prop-1-en-2-yl)phenyl]methanol for the construction of sulfonyl-containing tetrahydropyran and 1,3-dihydroisobenzofuran derivatives. Preliminary mechanistic studies show that the arylsulfonyl radical is the key intermediate in the reaction process.

Graphical abstract: Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide under photocatalysis

Supplementary files

Article information

Article type
Research Article
Submitted
30 מאי 2018
Accepted
03 יול 2018
First published
04 יול 2018

Org. Chem. Front., 2018,5, 2437-2441

Intramolecular oxysulfonylation of alkenes with the insertion of sulfur dioxide under photocatalysis

F. He, X. Cen, S. Yang, J. Zhang, H. Xia and J. Wu, Org. Chem. Front., 2018, 5, 2437 DOI: 10.1039/C8QO00528A

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