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Synthesis 2011(4): 662-668
DOI: 10.1055/s-0030-1258408
DOI: 10.1055/s-0030-1258408
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Substrate-Controlled Regioselective Cobalt(I)-Catalysed 1,4-Hydrovinylation Reactions
Further Information
Received
23 November 2010
Publication Date:
18 January 2011 (online)
Publication History
Publication Date:
18 January 2011 (online)
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Abstract
The substrate-directed regiochemistry of the cobalt-catalysed 1,4-hydrovinylation reaction is described. A variety of symmetrical and unsymmetrical 2,3-disubstituted 1,3-dienes are synthesised by ruthenium-catalysed enyne metathesis, and then reacted with a terminal alkene catalysed by cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane] [CoBr2(dppe)] under reductive conditions. The regiochemistry of the branched 1,4-diene products is influenced by the nature of the substituents on the unsymmetrical 2,3-disubstituted 1,3-dienes. The influence of steric and electronic effects is also discussed.
Key words
alkene - catalysis - cobalt - diene - regioselectivity
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