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Issue 34, 2018
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Influence of the catalyst structure in the cycloaddition of isocyanates to oxiranes promoted by tetraarylstibonium cations

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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-((dimethylamino)methyl)phenyl (6+). These new cationic antimony derivatives, along with the known [Ph4Sb]+ (1+), 1-naphthyltriphenylstibonium (2+), and [(Ant)SbPh3]+ (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 reactivities of 5+ and 6+ are hindered by the ancillary amino donor which quenches the Lewis acidity of the antimony center. A comparison of the other stibonium cations shows that 4+ is the most selective catalyst.

Graphical abstract: Influence of the catalyst structure in the cycloaddition of isocyanates to oxiranes promoted by tetraarylstibonium cations

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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., 2018,47, 11843-11850
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    Influence of the catalyst structure in the cycloaddition of isocyanates to oxiranes promoted by tetraarylstibonium cations

    M. Yang, N. Pati, G. Bélanger-Chabot, M. Hirai and F. P. Gabbaï, Dalton Trans., 2018, 47, 11843
    DOI: 10.1039/C8DT00702K

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