Arenediazonium o-Benzenedisulfonimides in Heck-Type Arylation of Allylic Alcohols

Margherita Barbero; Silvano Cadamuro; Stefano Dughera

doi:10.1055/s-2006-950245

PAPER

Arenediazonium o-Benzenedisulfonimides in Heck-Type Arylation of Allylic Alcohols

Margherita Barbero*, Silvano Cadamuro, Stefano Dughera
Dipartimento di Chimica Generale ed Organica Applicata, Università Torino, C.so Massimo D’Azeglio 48, 10125 Torino, Italy
Fax: +39(011)6707642; e-Mail: margherita.barbero@unito.it;

Abstract

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Abstract

Arenediazonium o-benzenedisulfonimides were reacted with primary and secondary allylic alcohols. The reactions, carried out in aqueous ethanol in the presence of palladium(II) acetate as precatalyst and sodium hydrogen carbonate as base, gave the arylation products with good overall conversion. In all cases, the major products were the β-arylated carbonyl derivatives. The o-benzenedisulfonimide was recovered in high yield from all the reactions, and it was recycled for the preparation of other salts.

Key words

allylic alcohols - arenediazonium salts - cross coupling - Heck reaction - arylations

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Referenzen

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