Copper-Catalyzed Coupling of Alkylamines and Aryl Iodides:  An Efficient System Even in an Air Atmosphere

Fuk Yee Kwong, Artis Klapars, and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
Org. Lett., 2002, 4 (4), pp 581–584
DOI: 10.1021/ol0171867
Publication Date (Web): January 18, 2002
Copyright © 2002 American Chemical Society

Abstract

Abstract Image

A mild method for the copper-catalyzed amination of aryl iodides is reported. This operationally simple C−N bond-forming protocol uses CuI as the catalyst and ethylene glycol as ligand in 2-propanol. A variety of functionalized aryl iodides as well as several amines were efficiently coupled using this method. This catalytic amination procedure is relatively insensitive to moisture and can be performed under an air atmosphere with comparable yield. Preliminary results on the amination of aryl bromides are also described.

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History

  • Published In Issue February 21, 2002
  • Received December 6, 2001

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