Ruthenium-catalyzed [2 + 2 + 1] Cocyclization of Isocyanates, Alkynes, and CO Enables the Rapid Synthesis of Polysubstituted Maleimides

Teruyuki Kondo,* Masato Nomura, Yasuyuki Ura, Kenji Wada, and Take-aki Mitsudo
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
J. Am. Chem. Soc., 2006, 128 (46), pp 14816–14817
DOI: 10.1021/ja066305g
Publication Date (Web): October 28, 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.

, teruyuki@scl.kyoto-u.ac.jp

Abstract

Abstract Image

Intermolecular [2 + 2 + 1] cocyclization of isocyanates, alkynes, and CO (1 atm) proceeded smoothly in the presence of a catalytic amount of Ru3(CO)12 (3.3 mol %) in mesitylene at 130 °C for 342 h to give a variety of polysubstituted maleimides in excellent yields with high selectivity. The reaction may involve an azaruthenacyclopentenone intermediate derived from oxidative cyclization of an isocyanate and an alkyne on an active ruthenium species.

Tools

History

  • Published In Issue November 22, 2006
  • Received August 30, 2006

Recommend & Share

Related Content

Other ACS content by these authors: