☆ 4.7 Article

Synthesis of δ-Bromo γ,δ-Unsaturated Carbonyl Compounds via Palladium-Catalyzed Bromoalkylation of Alkynoates

JOURNAL OF ORGANIC CHEMISTRY (2012)

期刊

JOURNAL OF ORGANIC CHEMISTRY

卷 77, 期 4, 页码 2029-2034

出版社

AMER CHEMICAL SOC

DOI: 10.1021/jo202416h

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Chemistry, Organic

资金

National Natural Science Foundation of China [20932002, 21172076]
National Basic Research Program of China (973 Program) [2011CB808600]
Guangdong Natural Science Foundation [10351064101000000]

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摘要

Palladium-catalyzed regio- and stereoselective intermolecular tandem reaction of electron-deficient alkynes, CuBr2, and allylic alcohol to synthesize delta-bromo-gamma,delta-unsaturated carbonyls was developed. A mechanism involving bromopalladation of alkyne, followed by insertion of allylic alcohol and allylic hydrogen shift, is proposed. The shift of allylic hydrogen is the rate-limiting step in this reaction.

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