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The Efficiency of the Metal Catalysts in the Nucleophilic Substitution of Alcohols is Dependent on the Nucleophile and Not on the Electrophile
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
2013 (English)In: Chemistry - An Asian Journal, ISSN 1861-4728, E-ISSN 1861-471X, Vol. 8, no 5, 974-981 p.Article in journal (Refereed) Published
Abstract [en]

In this study, we investigate the effect of the electrophiles and the nucleophiles for eight catalysts in the catalytic SN1 type substitution of alcohols with different degree of activation by sulfur-, carbon-, oxygen-, and nitrogen-centered nucleophiles. The catalysts do not show any general variance in efficiency or selectivity with respect to the alcohols and follow the trend of alcohol reactivity. However, when it comes to the nucleophile, the eight catalysts show general and specific variances in the efficiency and selectivity to perform the desired substitution. Interestingly, the selectivity of the alcohols to produce the desired substitution products was found to be independent of the electrophilicity of the generated carbocations but highly dependent on the ease of formation of the cation. Catalysts based on iron(III), bismuth(III), and gold(III) show higher conversions for S-, C-, and N-centered nucleophiles, and BiIII was the most efficient catalyst in all combinations. Catalysts based on rhenium(I) or rhenium(VII), palladium(II), and lanthanum(III) were the most efficient in performing the nucleophilic substitution on the various alcohols with the O-centered nucleophiles. These catalysts generate the symmetrical ether as a by-product from the reactions of S-, C-, and N-centered nucleophiles as well, resulting in lower chemoselectivity.

Place, publisher, year, edition, pages
2013. Vol. 8, no 5, 974-981 p.
National Category
Natural Sciences
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URN: urn:nbn:se:uu:diva-196660DOI: 10.1002/asia.201201178ISI: 000318235400018OAI: oai:DiVA.org:uu-196660DiVA: diva2:610672
Available from: 2013-03-12 Created: 2013-03-12 Last updated: 2017-12-06Bibliographically approved

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Biswas, SrijitSamec, Joseph

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