SO$_2$ conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling

Aurélien Adenot (1) , Joëlle Char (1) , Niklas von Wolff (1) , Guillaume Lefevre (1) , Lucile Anthore-Dalion (1) , Thibault Cantat (1)

1 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)

A sulfonylative Hiyama cross-coupling reaction using gaseous SO$_2$ is described, using Pd-catalysts. 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.

Domains: Catalysis; Organic chemistry

Aurélien Adenot, Joëlle Char, Niklas von Wolff, Guillaume Lefevre, Lucile Anthore-Dalion, et al.. SO$_2$ conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling. Chemical Communications, 2019, 55, pp.12924-12927. ⟨10.1039/C9CC06858A⟩. ⟨cea-02311034⟩