Insertion of Polar and Nonpolar Unsaturated Molecules into Carbon−Rhenium Bonds Generated by C−H Bond Activation:  Synthesis of Phthalimidine and Indene Derivatives

Yoichiro Kuninobu,* Yukimi Tokunaga, Atsushi Kawata, and Kazuhiko Takai*;
Contribution from the 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 (1), pp 202–209
DOI: 10.1021/ja054216i
Publication Date (Web): December 14, 2005
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 an aromatic aldimine with an isocyanate and an acetylene to give a phthalimidine and an indene derivative in a quantitative yield, respectively. The reactions proceed via C−H bond activation, insertion of the isocyanate or the acetylene, intramolecular nucleophilic cyclization to the aldimine of the generated amido− or alkenyl−rhenium species, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the insertion of a polar unsaturated molecule. This occurs more easily than the insertion of a nonpolar unsaturated molecule.

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History

  • Published In Issue January 11, 2006
  • Received June 26, 2005

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