期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 34, 页码 14232-14237出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja306323x
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资金
- National Institutes of Health [R01-GM62871]
- American Australian Association Merck Company Foundation Fellowship
- Endowed Fund for the Undergraduate Research Opportunities Program
- John Reed Fund
We have exploited a typically undesired elementary step in cross-coupling reactions, beta-hydride elimination, to accomplish palladium-catalyzed dehydrohalogenations of allcyl bromides to form terminal olefins. We have applied this method, which proceeds in excellent yield at room temperature in the presence of a variety of functional groups, to a formal total synthesis of (R)-mevalonolactone. Our mechanistic studies have established that the rate-determining step can vary with the structure of the alkyl bromide and, most significantly, that L2PdHBr (L = phosphine), an intermediate that is often invoked in palladium-catalyzed processes such as the Heck reaction, is not an intermediate in the active catalytic cycle.
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