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Reversible 1,1-hydroaluminations and C–H activation in reactions of a cyclic (alkyl)(amino) carbene with alane

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Abstract

Varying the reaction ratio of cyclic (alkyl)(amino) carbene (cAACEt) with AlH3·NEtMe2 leads to the isolation of (cAACEtH)AlH2·NEtMe2 1 and (cAACEtH)2Al(μ-H)2AlH2·NEtMe2 2 and the first example of a monomeric dialkyl-aluminum hydride (cAACEtH)2AlH 3. VT and 1H–1H EXSY NMR experiments of 3 demonstrated the isomerization of the diastereomers of 3 via the first instance of reversible hydride migration between the Al and the C center. In addition, heating solutions of 3 at 100 °C affords (cAACEtH)Al(CHC(Et)2CH2C(Me)2NC6H3(iPr)C(Me)CH2) 4 with loss of H2.

Graphical abstract: Reversible 1,1-hydroaluminations and C–H activation in reactions of a cyclic (alkyl)(amino) carbene with alane

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Publication details

The article was received on 22 Jun 2018, accepted on 03 Jul 2018 and first published on 03 Jul 2018


Article type: Communication
DOI: 10.1039/C8CC05013A
Citation: Chem. Commun., 2018, Advance Article
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    Reversible 1,1-hydroaluminations and C–H activation in reactions of a cyclic (alkyl)(amino) carbene with alane

    L. L. Cao and D. W. Stephan, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC05013A

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