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
J. Am. Chem. Soc., 2006, 128 (35), pp 11368–11369
DOI: 10.1021/ja064022i
Publication Date (Web): August 15, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kuninobu@cc.okayama-u.ac.jp, ; , ktakai@cc.okayama-u.ac.jp

Abstract

Abstract Image

A rhenium complex, [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 catalytic activity of the rhenium complex changes dramatically, and the insertion of acetylenes into a carbon−carbon single bond occurs under mild conditions. A plausible mechanism is that the reaction proceeds via the formation of a rhenacyclopentene intermediate, ring opening by a retro-aldol reaction, isomerization, and reductive elimination.

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History

  • Published In Issue September 06, 2006
  • Received June 8, 2006

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