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Pd-Catalyzed Carbonylation of Diazo Compounds at Atmospheric Pressure: A Catalytic Approach to Ketenes

Zhenhua Zhang, Yiyang Liu, Lin Ling, Yuxue Li, Yian Dong, Mingxing Gong, Xiaokun Zhao, Yan Zhang and Jianbo Wang*

*Beijing National Laboratory of Molecular Sciences (BNLMS), College of Chemistry, Peking University, Beijing 100871, China, Email: wangjbpku.edu.cn

Z. Zhang, Y. Liu, L. Ling, Y. Li, Y. Dong, M. Gong, X. Zhao, Y. Zhang, J. Wang, J. Am. Chem. Soc., 2011, 133, 4330-4341.

DOI: 10.1021/ja107351d (free Supporting Information)


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Abstract

Pd-catalyzed carbonylation of α-diazocarbonyl compounds or N-tosylhydrazone salts under atmospheric pressure of CO enables an efficient and mild approach toward ketene intermediates. These ketenes can react in situ with various nucleophiles to yield carboxylic acid derivates or in Staudinger cycloadditions to give β-lactam derivatives in good yields with excellent trans diastereoselectivity.

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Key Words

Staudinger Synthesis, β-Lactams, Carboxylation


ID: J48-Y2011-0780