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Cooperative N–H bond activation by amido-Ge(ii) cations

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Abstract

N-heterocyclic carbene (NHC) and tertiary phosphine-stabilized germylium-ylidene cations, [R(L)Ge:]+, featuring tethered amido substituents at R have been synthesized via halide abstraction. Characterization in the solid state by X-ray crystallography shows these systems to be monomeric, featuring a two-coordinate C,N- or P,N-ligated germanium atom. The presence of the strongly Lewis acidic cationic germanium centre and proximal amide function allows for facile cleavage of N–H bonds in 1,2-fashion: the products resulting from reactions with carbazole feature a tethered secondary amine donor bound to a three-coordinate carbazolyl-GeII centre. In each case, addition of the components of the N–H bond occurs to the same face of the germanium amide function, consistent with a coordination/proton migration mechanism. Such as sequence is compatible with the idea that substrate coordination via the pπ orbital at germanium reduces the extent of N-to-Ge π donation from the amide, thereby enhancing the basicity of the proximal N-group.

Graphical abstract: Cooperative N–H bond activation by amido-Ge(ii) cations

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Supplementary files

Article information


Submitted
01 Jun 2020
Accepted
24 Jun 2020
First published
25 Jun 2020

This article is Open Access

Dalton Trans., 2020, Advance Article
Article type
Paper

Cooperative N–H bond activation by amido-Ge(II) cations

X. Zhou, P. Vasko, J. Hicks, M. Á. Fuentes, A. Heilmann, E. L. Kolychev and S. Aldridge, Dalton Trans., 2020, Advance Article , DOI: 10.1039/D0DT01960G

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