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Regioselective C–H Bond Cleavage/Alkyne Insertion under Ruthenium Catalysis
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- Yuto Hashimoto
- Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
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- Koji Hirano
- Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
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- Tetsuya Satoh
- Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
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- Fumitoshi Kakiuchi
- JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
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- Masahiro Miura
- Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
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Description
The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C-H bond cleavage to produce the corresponding ortho-alkenylated products. Phenylpyrazoles and related substrates also underwent a similar coupling to give dialkenylated products selectively. Several competitive experiments were performed to obtain mechanistic insight into both the mono- and dialkenylation reactions.
Journal
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- The Journal of Organic Chemistry
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The Journal of Organic Chemistry 78 (2), 638-646, 2012-12-27
American Chemical Society (ACS)
