Synthesis of 3-Iodoindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Acetylenes, Followed by Electrophilic Cyclization

Dawei Yue, Tuanli Yao, and Richard C. Larock*
Department of Chemistry, Iowa State University, Ames, Iowa 50011
J. Org. Chem., 2006, 71 (1), pp 62–69
DOI: 10.1021/jo051549p
Publication Date (Web): December 6, 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.

, larock@iastate.edu

Abstract

Abstract Image

3-Iodoindoles have been prepared in excellent yields by coupling terminal acetylenes with N,N-dialkyl-o-iodoanilines in the presence of a Pd/Cu catalyst, followed by an electrophilic cyclization of the resulting N,N-dialkyl-o-(1-alkynyl)anilines using I2 in CH2Cl2. Aryl-, vinylic-, alkyl-, and silyl-substituted terminal acetylenes undergo this process to produce excellent yields of 3-iodoindoles. The reactivity of the carbon−nitrogen bond cleavage during cyclization follows the following order:  Me > n-Bu, Me > Ph, and cyclohexyl > Me. Subsequent palladium-catalyzed Sonogashira, Suzuki, and Heck reactions of the resulting 3-iodoindoles proceed smoothly in good yields.

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History

  • Published In Issue January 06, 2006
  • Received July 25, 2005

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