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Influence of the catalyst structure in the cycloaddition of oxiranes and isocyanates promoted by tetraarylstibonium cations

Abstract

In the context of our work on electron deficient group 15 cations as Lewis acid catalysts, we have synthesized the triflate salts of a series of tetraarylstibonium cations of general formula [ArSbPh3]+ with Ar = Mes (4+), o-(dimethylamino)phenyl (5+), and o-(dimethylaminomethyl)phenyl (6+). These new cationic antimony derivatives, along with the known [Ph4Sb]+ (1+), 1-naphthyltriphenylstibonium (2+), and [(Ant)SbPh3][OTf] (3+) have been evaluated as catalysts for the cycloaddition of oxiranes and isocyanates under mild conditions. While all stibonium cations favor the 3,4-oxazolidinone products, the reactivity of 5+ and 6+ are hindered by the ancillary amino donor which quenches the Lewis acidity of the antimony center. Overall, 4+ is found to be the most selective catalyst, a factor that we assign to the steric hindrance of the mesityl ligand.

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Publication details

The article was received on 21 Feb 2018, accepted on 20 Mar 2018 and first published on 22 Mar 2018


Article type: Paper
DOI: 10.1039/C8DT00702K
Citation: Dalton Trans., 2018, Accepted Manuscript
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    Influence of the catalyst structure in the cycloaddition of oxiranes and isocyanates promoted by tetraarylstibonium cations

    M. Yang, N. Pati, G. Bélanger-Chabot and F. P. Gabbaï, Dalton Trans., 2018, Accepted Manuscript , DOI: 10.1039/C8DT00702K

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