Issue 4, 2017

Copper(i)-catalyzed sulfonylative Suzuki–Miyaura cross-coupling

Abstract

Using a simple copper(I) catalyst has allowed a high yielding sulfonylative-Suzuki–Miyaura cross-coupling reaction to be developed. The process provides a single step route to diaryl sulfones from the direct combination of aryl boronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide is delivered from the surrogate reagent, DABSO. Variation of the reaction conditions allowed interruption of the sulfonylative-Suzuki coupling, resulting in the formation of a presumed Cu–sulfinate intermediate. These sulfinates could be trapped as their sodium salts and treated with electrophiles to allow access to arylalkyl sulfones, β-hydroxyl sulfones, sulfonamides and sulfonyl fluorides.

Graphical abstract: Copper(i)-catalyzed sulfonylative Suzuki–Miyaura cross-coupling

Supplementary files

Article information

Article type
Edge Article
Submitted
15 dec 2016
Accepted
16 feb 2017
First published
28 feb 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 3249-3253

Copper(I)-catalyzed sulfonylative Suzuki–Miyaura cross-coupling

Y. Chen and M. C. Willis, Chem. Sci., 2017, 8, 3249 DOI: 10.1039/C6SC05483H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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