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Synthesis of Propiolic Acids via Copper‐Catalyzed Insertion of Carbon Dioxide into the CH Bond of Terminal Alkynes
Author(s) -
Gooßen Lukas J.,
Rodríguez Nuria,
Manjolinho Filipe,
Lange Paul P.
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000564
Subject(s) - chemistry , catalysis , copper , carbon dioxide , phosphine , carbonate , caesium , triple bond , base (topology) , tris , terminal (telecommunication) , medicinal chemistry , polymer chemistry , organic chemistry , double bond , mathematical analysis , biochemistry , mathematics , telecommunications , computer science
A highly effective copper catalyst has been developed that promotes the insertion of carbon dioxide into the CH bond of terminal alkynes under unprecedentedly mild conditions. For the first time, propiolic acids can thus be synthesized in excellent yields from alkynes and carbon dioxide in the presence of the mild base cesium carbonate. The catalyst, (4,7‐diphenyl‐1,10‐phenanthroline)bis[tris(4‐fluorophenyl)phosphine]copper(I) nitrate, is easy accessible and relatively stable against air and water.