Journal
ACS CATALYSIS
Volume 4, Issue 12, Pages 4485-4489Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs501326p
Keywords
palladium; dehydrogenation; alkene; aryl halide; cross coupling
Categories
Funding
- Ministry of Science and Technology of the Republic of China [MOST-102-2633-M-007-002]
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A versatile palladium-catalyzed synthesis of highly substituted alpha,beta-unsaturated carbonyl compounds has been developed. In contrast to the known Heck-type coupling reaction of unsaturated carbonyl compounds with aryl halides, the present methodology allows the use of stable and readily available saturated carbonyl compounds as the alkene source. In addition, the reaction proceeds well with low catalyst loadings and does not require any expensive metal oxidants or ligands. A variety of saturated aldehydes, ketones, and esters are compatible for the reaction with aryl halides under the developed reaction conditions to afford alpha,beta-unsaturated carbonyl compounds in good to excellent yields. A possible reaction mechanism involves a palladium-catalyzed dehydrogenation followed by Heck-type cross couplings.
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