A RuH₂(CO)(PPh₃)₃-Catalyzed Regioselective Arylation of Aromatic Ketones with Arylboronates via Carbon-Hydrogen Bond Cleavage

Fumitoshi Kakiuchi,* Yusuke Matsuura, Shintaro Kan and Naoto Chatani

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, and PRESTO, JST, 4-1-8 Honcho Kawaguchi, Saitama, Japan, Email: kakiuchichem.eng.osaka-u.ac.jp

F. Kakiuchi, Y. Matsuura, S. Kan. N. Chatani, J. Am. Chem. Soc., 2005, 127, 5936-5945.

DOI: 10.1021/ja043334n

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Abstract

The ortho-arylation of aromatic ketones with arylboronates using RuH₂(CO)(PPh₃)₃ as a catalyst was conducted in pinacolone. This solvent dramatically suppressed the competing reduction of the aromatic ketones and, as a result, ortho-arylated products were obtained in high yield. The mechanism is discussed.

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Key Words

Biaryl Synthesis

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ID: J48-Y2005-2320