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 Cax 2018
Accepted
03 Qad 2018
First published
04 Qad 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements