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Synfacts 2010(4): 0465-0465  
DOI: 10.1055/s-0029-1219594
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Domino Palladium-Catalyzed Generation and Arylation of Sulfenate Anions

Contributor(s): Paul Knochel, Andreas J. Wagner
E. Bernoud, G. Le Duc, X. Bantreil, G. Prestat, D. Madec*, G. Poli*
Université Pierre et Marie Curie, Paris, France
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Publikationsdatum:
22. März 2010 (online)

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Significance

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