Brønsted Acid Catalyzed Addition of Phenols, Carboxylic Acids, and Tosylamides to Simple Olefins

Zigang Li, Junliang Zhang, Chad Brouwer, Cai-Guang Yang, Nicholas W. Reich, and Chuan He*
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637
Org. Lett., 2006, 8 (19), pp 4175–4178
DOI: 10.1021/ol0610035
Publication Date (Web): August 18, 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.

, chuanhe@uchicago.edu

Abstract

Abstract Image

Intermolecular addition of phenols, carboxylic acids, and protected amines to inert olefins can be catalyzed by low concentrations (1−5%) of triflic acid. Functional groups, such as the methoxyl substitution on aromatics, could be tolerated if the concentration of triflic acid and the reaction temperature are controlled appropriately. This reaction provides one of the simplest olefin addition methods and is an alternative to metal-catalyzed reactions.

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History

  • Published In Issue September 14, 2006
  • Received April 26, 2006

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