Pd-Catalyzed Carbonylative Reactions of Aryl Iodides and Alkynyl Carboxylic Acids via Decarboxylative Couplings

Alkynyl carboxylic acids reacted with aryl iodides under a CO atmosphere in the presence of a palladium catalyst to produce α,β-alkynyl aryl ketones in good yields. The maximum turnover number was 16 800. The desired carbonylative coupling was formed from phenyl propiolic acid without any formation...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 5; pp. 944 - 947
Main Authors Park, Ahbyeol, Park, Kyungho, Kim, Yong, Lee, Sunwoo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.03.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
VINYLIC HALIDES
PALLADIUM
KETONES
BENZYL
ACYL CHLORIDES
SONOGASHIRA REACTION
AMIDATION
TERMINAL ALKYNES
DIARYLALKYNES
WATER
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Summary:Alkynyl carboxylic acids reacted with aryl iodides under a CO atmosphere in the presence of a palladium catalyst to produce α,β-alkynyl aryl ketones in good yields. The maximum turnover number was 16 800. The desired carbonylative coupling was formed from phenyl propiolic acid without any formation of a noncarbonylative coupling product in the absence of CuI. However, the reaction with alkyl-substituted alkynyl carboxylic acids required CuI as a cocatalyst for high yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102993y