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Synthesis 2009(19): 3305-3310  
DOI: 10.1055/s-0029-1216900
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Cobalt-Catalysed [6+2] Cycloaddition of Internal Alkynes and Terminal ­Alkenes with Cycloheptatriene

Gerhard Hilt*, Anna Paul, Christoph Hengst
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein Straße, 35043 Marburg, Germany
Fax: +49(6421)2825677; e-Mail: Hilt@chemie.uni-marburg.de;
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Publication History

Received 12 May 2009
Publication Date:
10 July 2009 (online)

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Abstract

The cobalt-catalysed [6+2] cycloaddition of cycloheptatriene with internal alkynes as well as with terminal alkenes is described. The cycloaddition process is most efficiently catalysed by cobalt dibromide[bis(triisopropylphosphite)] complexes in dichloromethane as the solvent of choice. In the cobalt-catalysed reaction of cycloheptatriene with norbornene an unexpected tricyclic [2+2] cycloaddition product was isolated in excellent yields.

Key words

alkyne - alkene - cobalt - cycloaddition - dienes

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8

dppp: 1,3-bis(diphenylphosphino)propane;
dppb: 1,4-bis(diphenylphosphino)butane;
dpph: 1,6-bis(diphenylphosphino)hexane;
dppf: 1,1′-bis(diphenylphosphino)ferrocene.