Synthesis of Terminal Allenes via a Copper-Catalyzed Decarboxylative Coupling Reaction of Alkynyl Carboxylic Acids

Synthesis of terminal allenes via a copper-catalyzed decarboxylative coupling reaction was developed. Aryl alkynyl carboxylic acid, paraformaldehyde, and dicyclohexylamine were reacted with CuI (20 mol %) in diglyme at 100 °C for 2 h to produce the terminal allene in moderate to good yields. The met...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-01, Vol.81 (1), p.303-308
Main Authors: Lim, Jeongah, Choi, Jinseop, Kim, Han-Sung, Kim, In Seon, Nam, Kye Chun, Kim, Jimin, Lee, Sunwoo
Format: Article
Language:English
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Summary:Synthesis of terminal allenes via a copper-catalyzed decarboxylative coupling reaction was developed. Aryl alkynyl carboxylic acid, paraformaldehyde, and dicyclohexylamine were reacted with CuI (20 mol %) in diglyme at 100 °C for 2 h to produce the terminal allene in moderate to good yields. The method showed good functional group tolerance.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02361