Rhenium-Catalyzed Formation of Indene Frameworks via C−H Bond Activation:  [3+2] Annulation of Aromatic Aldimines and Acetylenes

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., 2005, 127 (39), pp 13498–13499
DOI: 10.1021/ja0528174
Publication Date (Web): September 8, 2005
Copyright © 2005 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 an aromatic aldimine with an acetylene to give an indene derivative in a quantitative yield. The reaction proceeds via C−H bond activation, insertion of the acetylene, intramolecular nucleophilic cyclization, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the intramolecular nucleophilic cyclization of the alkenylmetal species generated by insertion of the acetylene.

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  • Published In Issue October 05, 2005
  • Received April 29, 2005

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