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Review | Regular issue | Vol 85, No. 5, 2012, pp.1017-1043
Published online, 22nd February, 2012
DOI: 10.3987/REV-12-729
Rhodium-Catalyzed [2+2+2] Cycloaddition for the Synthesis of Substituted Pyridines, Pyridones, and Thiopyranimines

Ken Tanaka*

*Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo184-8588, Japan

Abstract

The transition-metal-catalyzed [2+2+2] cycloaddition of alkynes with nitriles is a useful and atom-economical method for the synthesis of substituted pyridines. The use of isocyanates and isothiocyanates in place of nitriles affords substituted pyridones and thiopyranimines, respectively. This review comprehensively covers the [2+2+2] cycloaddition reactions catalyzed by rhodium complexes for the synthesis of substituted pyridines, pyridones, and thiopyranimines. Asymmetric variants of these rhodium-catalyzed [2+2+2] cycloaddition reactions are also described.