Efficient Catalytic Insertion of Acetylenes into a Carbon-Carbon Single Bond of Nonstrained Cyclic Compounds under Mild Conditions

Yoichiro Kuninobu,* Atsushi Kawata and Kazuhiko Takai*

*Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan, Email: kuninobucc.okayama-u.ac.jp, ktakaicc.okayama-u.ac.jp

Y. Kuninobu, A. Kawata, K. Takai, J. Am. Chem. Soc., 2006, 128, 11368-11369.

DOI: 10.1021/ja064022i

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Abstract

[ReBr(CO)₃(thf)]₂ catalyzes the reaction of a 1,3-dicarbonyl cyclic compound with an acetylene to give a medium-sized cyclic compound in excellent yield. By using isocyanide as an additive, the insertion of acetylenes into a carbon-carbon single bond occurs under mild conditions.

see article for more examples

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Rhenium-Catalyzed Insertion of Terminal Acetylenes into a C-H Bond of Active Methylene Compounds

Y. Kuninobu, A. Kawata, K. Takai, Org. Lett., 2005, 7, 4823-4825.

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Key Words

ring expansion, cyclic ketones, cycoalkenes

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ID: J48-Y2006-2920