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Synthesis 2006(20): 3443-3452
DOI: 10.1055/s-2006-950245
DOI: 10.1055/s-2006-950245
PAPER
© Georg Thieme Verlag Stuttgart · New York
Arenediazonium o-Benzenedisulfonimides in Heck-Type Arylation of Allylic Alcohols
Further Information
Received
31 May 2006
Publication Date:
10 October 2006 (online)
Publication History
Publication Date:
10 October 2006 (online)
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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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