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Issue 2, 2010
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Bis(oxazolinyl)phenylborane: A Lewis acid-containing ligand for methide abstraction-based coordination to aluminum(III)

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Abstract

A compound that contains a Lewis acidic boron center and coordinating oxazoline groups, bis(4,4-dimethyl-2-oxazolinyl)phenylborane (PhB(OxMe2)2; 1), has been prepared and spectroscopically characterized. Solvent dependent 15N and 11B NMR spectroscopic properties and solid-state 11B NMR measurements provide support for intermolecular interactions involving Lewis acid and base sites. The bifunctional nature of oxazolinylborane 1 is demonstrated by its reaction with (AlMe3)2, which proceeds via methide abstraction by the boron and oxazoline coordination to aluminum to yield [2-PhMeB(OxMe2)2AlMe2] (2). Compound 2 contains a planar six-membered chelate ring, in contrast to related bis(pyrazolyl)boratoaluminum compounds that are puckered. Additionally, compound 2 and related bidentate tris(oxazolinyl)phenylborato dimethylaluminum are inert toward aluminum-methyl bond protonolysis. This robust nature suggested the possibility of using these oxazolinylboratoaluminum compounds in catalytic reactions, as is demonstrated by lactide ring-opening polymerization.

Graphical abstract: Bis(oxazolinyl)phenylborane: A Lewis acid-containing ligand for methide abstraction-based coordination to aluminum(III)

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Publication details

The article was received on 17 Jun 2009, accepted on 21 Sep 2009 and first published on 27 Oct 2009


Article type: Paper
DOI: 10.1039/B911851A
Citation: Dalton Trans., 2010,39, 641-653
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    Bis(oxazolinyl)phenylborane: A Lewis acid-containing ligand for methide abstraction-based coordination to aluminum(III)

    J. F. Dunne, K. Manna, J. W. Wiench, A. Ellern, M. Pruski and A. D. Sadow, Dalton Trans., 2010, 39, 641
    DOI: 10.1039/B911851A

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