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Efficient and Selective Formation of Unsaturated Carboxylic and Phenylacetic Acids from Diketene
Author(s) -
Mori Takamichi,
Akioka Yusuke,
Kawahara Hisaho,
Ninokata Ryo,
Onodera Gen,
Kimura Masanari
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201404816
Subject(s) - diketene , chemistry , cycloaddition , alkyne , catalysis , methylene , nickel , medicinal chemistry , organic chemistry , combinatorial chemistry
A nickel catalyst promotes the multicomponent coupling reaction of diketene, an alkyne, and Me 2 Zn to provide 3‐methylene‐4‐hexenoic acids in excellent yields. Under similar conditions, the combination of the nickel catalyst and Et 2 Al(OEt) promotes a cycloaddition reaction involving dimerization of an alkyne to furnish phenylacetic acids. In the presence of PPh 3 , a formal [2+2+1+1] cycloaddition reaction proceeds to afford regioisomeric phenylacetic acids via cleavage of the CC bond.