期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 1, 页码 36-56出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404070
关键词
alkenes; catalysis; nucleophilic addition; palladium; stereochemistry
资金
- Swedish Research Council
- European Research Council [ERC AdG 247014]
- Wenner-Gren Foundation
In this review the stereochemistry of palladium-catalyzed addition of nucleophiles to alkenes is discussed, and examples of these reactions in organic synthesis are given. Most of the reactions discussed involve oxygen and nitrogen nucleophiles; the Wacker oxidation of ethylene has been reviewed in detail. An anti-hydroxypalladation in the Wacker oxidation has strong support from both experimental and computational studies. From the reviewed material it is clear that anti-addition of oxygen and nitrogen nucleophiles is strongly favored in intermolecular addition to olefin-palladium complexes even if the nucleophile is coordinated to the metal. On the other hand, syn-addition is common in the case of intramolecular oxy- and amidopalladation as a result of the initial coordination of the internal nucleophile to the metal.
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