Efficient and Selective Formation of Unsaturated Carboxylic and Phenylacetic Acids from Diketene |
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Authors: | Takamichi Mori Yusuke Akioka Hisaho Kawahara Ryo Ninokata Dr. Gen Onodera Prof. Dr. Masanari Kimura |
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Affiliation: | Graduate School of Engineering, Nagasaki University, 1‐14 Bunkyo machi, Nagasaki 852‐8521 (Japan) http://www.cms.nagasaki‐u.ac.jp/lab/yuuki/index.html |
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Abstract: | A nickel catalyst promotes the multicomponent coupling reaction of diketene, an alkyne, and Me2Zn to provide 3‐methylene‐4‐hexenoic acids in excellent yields. Under similar conditions, the combination of the nickel catalyst and Et2Al(OEt) promotes a cycloaddition reaction involving dimerization of an alkyne to furnish phenylacetic acids. In the presence of PPh3, a formal [2+2+1+1] cycloaddition reaction proceeds to afford regioisomeric phenylacetic acids via cleavage of the C?C bond. |
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Keywords: | carboxylic acids cycloaddition nickel synthetic methods zinc |
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