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Sulfonylative Hiyama Cross-Coupling: Development and Mechanistic Insights

A Adenot 1 J Char 1 N von Wolff 1 G Lefèvre 1 T Cantat 1
1 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
Abstract : Due to distinctive structural and electronic features, sulfones have attracted a particular attention over the pa st few decades, ma king it a widespread functional group.[1] Present in many contemporary pharmaceuticals and agrochemicals, they are also used as essential intermediates in organic synthesis. Therefore, numérous methodologies have been developed for their preparation. [1] However, the most common methods suffer from significant limitations with harsh reaction conditions or regioselectivity issues. Recently, the insertion of a molecule of sulfur dioxide between two partners was investigated and reactions involving organomagnesium,[2a] organozind2b] and organoboron[2c] compounds were reported. Herein we report a direct single-step palladium-catalyzed synthesis of sulfones involving organosilanes, sulfur dioxide and organohalides. Different mechanistic pathways were envisaged and discussed both from an experimental and theoretical stand point.
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https://hal-cea.archives-ouvertes.fr/cea-02329659
Contributor : Serge Palacin <>
Submitted on : Wednesday, October 23, 2019 - 4:14:09 PM
Last modification on : Monday, February 10, 2020 - 6:13:58 PM
Long-term archiving on: : Friday, January 24, 2020 - 7:38:04 PM

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A Adenot, J Char, N von Wolff, G Lefèvre, T Cantat. Sulfonylative Hiyama Cross-Coupling: Development and Mechanistic Insights. GECOM-CONCOORD 2019, May 2019, Erquy, France. ⟨cea-02329659⟩

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