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Sulfonylative Hiyama Cross-Coupling: Development and Mechanistic Insights

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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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cea-02329659 , version 1 (23-10-2019)

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  • HAL Id : cea-02329659 , version 1

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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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