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An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
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2016 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 7, 2481-2486 p.Article in journal (Refereed) PublishedText
Abstract [en]

In this study, [Fe(dibm)(3)] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2016. Vol. 22, no 7, 2481-2486 p.
Keyword [en]
alkylation, carbohydrates, green chemistry, iron, regioselectivity
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-183312DOI: 10.1002/chem.201504477ISI: 000369855000036PubMedID: 26789016ScopusID: 2-s2.0-84961285717OAI: diva2:910580

QC 20160309

Available from: 2016-03-09 Created: 2016-03-07 Last updated: 2016-03-19Bibliographically approved

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