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Nickel-Catalyzed Selective Conversion of Two Different Aldehydes to Cross-Coupled Esters

Yoichi Hoshimoto, Masato Ohashi and Sensuke Ogoshi*

*Department of Applied Chemistry, Faculty of Engineering, and Center for Atomic and Molecular Technologies, Osaka University, Suita, Osaka 565-0871, Japan, Email: ogoshichem.eng.osaka-u.ac.jp

Y. Hoshimoto, M. Ohashi, S. Ogoshi, J. Am. Chem. Soc., 2011, 133, 4668-4671.

DOI: 10.1021/ja109908x (free Supporting Information)


Abstract

In the presence of a Ni(0)/NHC catalyst, an equimolar mixture of various aliphatic and aryl aldehydes can selectively be converted to single cross-coupled ester. The reaction represents 100% atom efficiency and generates no waste. Mechanistic studies have revealed that the striking feature is the simultaneous coordination of two aldehydes to Ni(0).

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Key Words

Tishchenko Reaction


ID: J48-Y2011-0830