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Synthesis 2002(5): 0609-0618
DOI: 10.1055/s-2002-23549
PAPER
© Georg Thieme Verlag Stuttgart · New York

Cobalt(I)-catalyzed 1,4-Hydrovinylation Reactions of 1,3-Dienes withFunctionalized Terminal Alkenes under Mild Conditions

Gerhard Hilt*, Steffen Lüers
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München, Germany
Fax: +49(89)21807425; e-Mail: Gerhard.Hilt@cup.uni-muenchen.de;
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Publication History

Received 12 February 2002
Publication Date:
02 April 2002 (online)

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Abstract

The cobalt-catalyzed 1,4-hydrovinylation of acyclic 1,3-dienes with various functionalized terminal alkenes is described. The mild reaction conditions are significant because they considerably reduce the amount of side products and for non acceptor-substituted alkenes the branched products are formed exclusively. The CoBr2(dppe) catalyst system controls the regiochemistry of the hydrovinylation process. Unsymmetrical 1,3-dienes yield products, where the new carbon-carbon bond is formed at the less substituted end of the 1,3-diene.

Key words

cobalt - 1,4-hydrovinylation reaction - alkene - 1,3-diene - 1,4-diene

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