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. 2010 Jan 15;12(2):320-3.
doi: 10.1021/ol902620t.

Aryl sulfoxides from allyl sulfoxides via [2,3]-sigmatropic rearrangement and domino Pd-catalyzed generation/arylation of sulfenate anions

Elise Bernoud  1 , Gaëtan Le Duc, Xavier Bantreil, Guillaume Prestat, David Madec, Giovanni Poli
Affiliations

Aryl sulfoxides from allyl sulfoxides via [2,3]-sigmatropic rearrangement and domino Pd-catalyzed generation/arylation of sulfenate anions

Elise Bernoud et al. Org Lett. .

Abstract

Allylic sulfoxides, via [2,3]-sigmatropic rearrangement and oxidative addition of the resulting allylic sulfenate esters to Pd(0), are found to be excellent precursors of sulfenate anions. This hitherto unknown reactivity is applied in a new Pd(0)-catalyzed domino sequence involving sulfenate anion generation followed by arylation to afford aryl sulfoxides.

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