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The syn/anti-Dichotomy in the Palladium-Catalyzed Addition of Nucleophiles to Alkenes
Stockholm University, Faculty of Science, Department of Organic Chemistry. Academy of Sciences of the Czech Republic, Czech Republic; Charles University, Czech Republic.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2015 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 21, no 51, 36-56 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2015. Vol. 21, no 51, 36-56 p.
Keyword [en]
alkenes, catalysis, nucleophilic addition, palladium, stereochemistry
National Category
Organic Chemistry
URN: urn:nbn:se:su:diva-113544DOI: 10.1002/chem.201404070ISI: 000346735000001OAI: diva2:787081


Available from: 2015-02-09 Created: 2015-02-04 Last updated: 2015-02-09Bibliographically approved

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Kocovsky, PavelBäckvall, Jan-E.
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