β-Oxo Amides: Inexpensive and Efficient Ligands for the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction

Jin-Heng Li; Yue-Hua Zhang; Ren-Jie Song; Ye-Xiang Xie; Chen-Liang Deng; Yun Liang

doi:10.1055/s-2007-983891

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Synthesis 2007(19): 2957-2966
DOI: 10.1055/s-2007-983891

PAPER

β-Oxo Amides: Inexpensive and Efficient Ligands for the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction

Jin-Heng Li*, Yue-Hua Zhang, Ren-Jie Song, Ye-Xiang Xie, Chen-Liang Deng, Yun Liang
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(731)8872531; e-Mail: jhli@hunnu.edu.cn;

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Publication History

Received 11 May 2007
Publication Date:
11 September 2007 (online)

Abstract
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Abstract

β-Oxo amides were found to be inexpensive and efficient ligands for the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. In the presence of palladium(II) acetate and N-(4-methoxyphenyl)-3-oxobutanamide (L7), a variety of aryl halides, including deactivated aryl chlorides and heteroaryl halides, were successfully coupled to arylboronic acids in moderate to excellent yields providing very high turnover numbers (maximum TON <950,000 and TOF <79,167). It is noteworthy that the reaction is conducted under mild and aerobic conditions.

Key words

palladium(II) acetate - β-oxo amide - Suzuki-Miyaura cross-coupling reaction - aryl halides - arylboronic acids

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