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Issue 67, 2018
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Metal nitrene-like reactivity of a Si[double bond, length as m-dash]N bond towards CO2

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Abstract

The unusual reactivity of the Si[double bond, length as m-dash]N bond in metallo-iminosilane [DippN = Si(OSiMe3)Ni(Cl)(NHC)2] 1 towards CO2 and cyclohexyl isocyanate (CyNCO) is reported; it reacts with two molar equiv. of CO2 to give the [2+2+2] cycloaddition product 3 with complete scission of the σ- and π-Si–N bonds akin to transition-metal nitrene complexes. Theoretical calculations indicate that this reaction is made viable by the high polarity of the Si–N interaction in the intermediary [2+2] cycloaddition product 2, which could also be crystallographically characterised. In the case of isocyanate, the [2+2] cycloaddition product of the C[double bond, length as m-dash]O and Si[double bond, length as m-dash]N bonds is formed exclusively.

Graphical abstract: Metal nitrene-like reactivity of a Si [[double bond, length as m-dash]] N bond towards CO2

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Publication details

The article was received on 29 Jun 2018, accepted on 30 Jul 2018 and first published on 30 Jul 2018


Article type: Communication
DOI: 10.1039/C8CC05238G
Chem. Commun., 2018,54, 9352-9355

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    Metal nitrene-like reactivity of a Si[double bond, length as m-dash]N bond towards CO2

    T. J. Hadlington, T. Szilvási and M. Driess, Chem. Commun., 2018, 54, 9352
    DOI: 10.1039/C8CC05238G

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