Addition of Grignard Reagents to Aryl Acid Chlorides:  An Efficient Synthesis of Aryl Ketones

Xiao-jun Wang,* Li Zhang, Xiufeng Sun, Yibo Xu, Dhileepkumar Krishnamurthy, and Chris H. Senanayake
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877
Org. Lett., 2005, 7 (25), pp 5593–5595
DOI: 10.1021/ol052150q
Publication Date (Web): November 8, 2005
Copyright © 2005 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.

, xwang@rdg.boehringer-ingelheim.com

Abstract

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Direct addition of Grignard reagents to acid chlorides in the presence of bis[2-(N,N-dimethylamino)ethyl] ether proceeds selectively to provide aryl ketones in high yields. A possible tridentate interaction between Grignard reagents and bis[2-(N,N-dimethylamino)ethyl] ether moderates the reactivity of Grignard reagents, preventing the newly formed ketones from nucleophilic addition by Grignard reagents.

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History

  • Published In Issue December 08, 2005
  • Received September 6, 2005

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