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SO2 conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling

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Abstract

A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion.

Graphical abstract: SO2 conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling

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Publication details

The article was received on 03 Sep 2019, accepted on 03 Oct 2019 and first published on 08 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC06858A
Chem. Commun., 2019, Advance Article

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    SO2 conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling

    A. Adenot, J. Char, N. von Wolff, G. Lefèvre, L. Anthore-Dalion and T. Cantat, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC06858A

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