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Issue 94, 2016
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Catalytic dehydrocoupling of amines and boranes by an incipient tin(II) hydride

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Abstract

The facile heterodehydrocoupling of a range of primary or secondary amines and even ammonia with pinacolborane (HBPin) was accomplished using {ArMe6Sn(μ-OMe)}2 (1, ArMe6 = C6H3-2,6-(C6H2-2,4,6-Me3)2) as pre-catalysts for a catalytically active tin(II) hydride. The more sterically hindered pre-catalyst 2, {AriPr4Sn(μ-OMe)}2 (AriPr4 = C6H3-2,6-(C6H3-2,6-iPr2)2) facilitated the dehydrocoupling only of primary amines with HBPin, and at an increased rate relative to the less crowded {ArMe6Sn(μ-OMe)}2. Also presented is {ArMe6Sn(μ-NEt2)}2 (3), which can be converted into the structurally characterizable {ArMe6Sn(μ-NEt2)(μ-H)SnArMe6} (4) via the addition of pinacol borane. This, alongside stoichiometric studies, give insight into the mechanism of the catalysis.

Graphical abstract: Catalytic dehydrocoupling of amines and boranes by an incipient tin(ii) hydride

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Publication details

The article was received on 24 Aug 2016, accepted on 22 Sep 2016 and first published on 22 Sep 2016


Article type: Communication
DOI: 10.1039/C6CC06963K
Citation: Chem. Commun., 2016,52, 13656-13659
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    Catalytic dehydrocoupling of amines and boranes by an incipient tin(II) hydride

    J. D. Erickson, T. Y. Lai, D. J. Liptrot, M. M. Olmstead and P. P. Power, Chem. Commun., 2016, 52, 13656
    DOI: 10.1039/C6CC06963K

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