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Synthesis 2008(10): 1523-1526  
DOI: 10.1055/s-2008-1072569
PAPER
© Georg Thieme Verlag Stuttgart · New York

Tetrabutylammonium Pyridin-2-olate: A New Reagent for the Efficient Synthesis of N-Aryl Pyridin-2-ones

Huiping Zhang*, Bang-Chi Chen, Bei Wang, Sam T. Chao, Rulin Zhao, Ngiapkie Lim, Balu Balasubramanian
Discovery Chemistry, Bristol-Myers Squibb Research and Development, Princeton, NJ 08543, USA
Fax: +1(609)2526804; e-Mail: huiping.zhang@bms.com;
Further Information

Publication History

Received 28 November 2007
Publication Date:
27 March 2008 (online)

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Abstract

A new reagent, tetrabutylammonium pyridin-2-olate, was prepared and its application to the efficient synthesis of N-aryl pyridine-2-ones was demonstrated using CuI-catalyzed coupling reactions with aryl iodides. This coupling reaction is mild, high-yielding, and remarkably chemoselective (N- vs. O-arylation). It is also compatible with substrates containing labile functional groups.

Key words

preparation - tetrabutylammonium pyridin-2-olate - aryl iodides - CuI-catalyzed coupling reaction - N-aryl pyridin-2-ones

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17

A similar low yield (22%) was reported by Filipski and coworkers for the copper-catalyzed coupling reaction of pyridin-2(1H)-one with methyl 4-iodobenzoate, see ref 12e.