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

Aurélien Adenot; Joëlle Char; Niklas von Wolff; Guillaume Lefevre; Lucile Anthore-Dalion; Thibault Cantat

doi:10.1039/C9CC06858A

Journal articles

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, *}

* Corresponding author

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 : 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.

Document type :

Journal articles

Domain :

Chemical Sciences / Catalysis

Chemical Sciences / Organic chemistry

Complete list of metadatas

Cited literature [18 references] Display Hide Download

https://hal-cea.archives-ouvertes.fr/cea-02311034
Contributor : Serge Palacin <>
Submitted on : Thursday, October 10, 2019 - 4:11:20 PM
Last modification on : Monday, December 14, 2020 - 3:42:35 PM

Adenot_ChemComm2019_V0.pdf

Files produced by the author(s)

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

File

Identifiers

Collections

Citation

Export

Metrics

127

235

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

File

Identifiers

Collections

Citation

Export

Share

Metrics

127

235