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Issue 4, 2017
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Copper(I)-catalyzed sulfonylative Suzuki–Miyaura cross-coupling

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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

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Publication details

The article was received on 15 Dec 2016, accepted on 16 Feb 2017 and first published on 28 Feb 2017


Article type: Edge Article
DOI: 10.1039/C6SC05483H
Citation: Chem. Sci., 2017,8, 3249-3253
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    Copper(I)-catalyzed sulfonylative Suzuki–Miyaura cross-coupling

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

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