Synlett 2005(13): 2062-2066  
DOI: 10.1055/s-2005-871959
LETTER
© Georg Thieme Verlag Stuttgart · New York

Thermal and Au(I)-Catalyzed Intramolecular [4+2] Cycloaddition of Aryl-Substituted 1,6-Diynes for the Synthesis of Biaryl Compounds

Takanori Shibata*, Ryo Fujiwara, Daisuke Takano
Department of Chemistry, School of Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan
e-Mail: tshibata@waseda.jp;
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Publikationsverlauf

Received 17 May 2005
Publikationsdatum:
13. Juli 2005 (online)

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Abstract

1,6-Diynes, possessing aryl groups on their termini, undergo an intramolecular [4+2] cycloaddition via strained cyclic allene intermediates to give various biaryl compounds. Under thermal conditions, isomerization of the intermediates occurs, while, in the presence of a cationic gold catalyst, skeletal rearrangement is a ­major pathway.