Issue 13, 2023

Copper-catalyzed ring-opening sulfonylation of cyclopropanols via the insertion of sulfur dioxide toward the synthesis of γ-keto aryl sulfones

Abstract

A copper-catalyzed three-component sulfonylation reaction that employs cyclopropanols, aryldiazonium tetrafluoroborates, and sulfur dioxide (SOgen) is presented. This protocol provides easy and straightforward access to structurally diverse γ-keto aryl sulfones with good yields, mild reaction conditions, low catalyst loading, and good functional group tolerance. Furthermore, this method was successfully applied in a gram-scale reaction, highlighting its robustness and potential. Preliminary mechanistic experiments suggest that a radical process may be involved in this transformation.

Graphical abstract: Copper-catalyzed ring-opening sulfonylation of cyclopropanols via the insertion of sulfur dioxide toward the synthesis of γ-keto aryl sulfones

Supplementary files

Article information

Article type
Research Article
Submitted
12 Apr 2023
Accepted
22 May 2023
First published
23 May 2023

Org. Chem. Front., 2023,10, 3239-3244

Copper-catalyzed ring-opening sulfonylation of cyclopropanols via the insertion of sulfur dioxide toward the synthesis of γ-keto aryl sulfones

L. Shen, X. Zhang and Z. Lian, Org. Chem. Front., 2023, 10, 3239 DOI: 10.1039/D3QO00552F

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