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Issue 20, 2017, Issue in Progress
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Exploring the catalytic activity of Lewis-acidic uranyl complexes in the nucleophilic acyl substitution of acid anhydrides

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Abstract

The catalytic activities of several uranyl complexes, such as N,N′-disalicylidene-o-phenelyenediaminato(ethanol)dioxouranium(VI) (UO2(salophen)EtOH), bis(dibenzoylmethanato)(ethanol)dioxouranium(VI) (UO2(dbm)2EtOH), pentakis(N,N-dimethylformamide)dioxouranium(VI) ([UO2(DMF)5]2+), and tetrakis(triphenylphosphine oxide)dioxouranium(VI) ([UO2(OPPh3)4]2+), were examined in the nucleophilic acyl substitution of acid anhydrides. Among them, [UO2(OPPh3)4]2+ was the most efficient to give ethyl acetate and acetic acid from acetic anhydride (Ac2O) and ethanol, and was resistant towards decomposition during the catalytic reaction. Several nucleophiles were also subjected to the catalytic acylation reaction using acetic and pivalic anhydride. Kinetic and spectroscopic studies suggested that [UO2(OPPh3)4]2+ interacts with Ac2O to form [UO2(Ac2O)(OPPh3)3]2+. Interaction of this actual catalyst with additional Ac2O determines the rate of the overall nucleophilic acyl substitution reaction.

Graphical abstract: Exploring the catalytic activity of Lewis-acidic uranyl complexes in the nucleophilic acyl substitution of acid anhydrides

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Supplementary files

Article information


Submitted
05 Dec 2016
Accepted
08 Feb 2017
First published
21 Feb 2017

This article is Open Access

RSC Adv., 2017,7, 12201-12207
Article type
Paper

Exploring the catalytic activity of Lewis-acidic uranyl complexes in the nucleophilic acyl substitution of acid anhydrides

K. Takao and S. Akashi, RSC Adv., 2017, 7, 12201
DOI: 10.1039/C6RA27796A

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