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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, Email: xwangrdg.boehringer-ingelheim.com

X.-J. Wang, L. Zhang, X. Sun, Y. Xu, D. Krishnamurthy, C. H. Senanayake, Org. Lett., 2005, 7, 5593-5595.

DOI: 10.1021/ol052150q (free Supporting Information)


 

Abstract

A possible tridentate complex between Grignard reagents and bis[2-(N,N-dimethylamino)ethyl] ether moderates the reactivity of the Grignard reagents and enables the selective reaction with acid chlorides to provide aryl ketones in high yield without a subsequent second nucleophilic addition.

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Key Words

Grignard Reagents, Acylation


ID: J54-Y2005-2070