Issue 7, 2024

Synthesis and reactivity of N-heterocyclic carbene (NHC)-supported heavier nitrile ylides

Abstract

The synthesis and isolation of stable heavier analogues of nitrile ylide as N-heterocyclic carbene (NHC) adducts of phosphasilenyl-tetrylene [(NHC)(TerAr)Si(H)PE14(TerAr)] (E14 = Ge 1, Sn 2; TerAr = 2,6-Mes2C6H3, NHC = IMe4) are reported. The delocalized Si–P–E14 π-conjugation was examined experimentally and computationally. Interestingly, the germanium derivative 1 exhibits a 1,3-dipolar nature, leading to an unprecedented [3 + 2] cycloaddition with benzaldehyde, resulting in unique heterocycles containing four heteroatoms from group 14, 15, and 16. Further exploiting the nucleophilicity of germanium, activation of the P–P bond of P4 was achieved, leading to a [(NHC)(phosphasilenyl germapolyphide)] complex. Moreover, the [3 + 2] cycloaddition and the σ-bond activation by 1 resemble the characteristics of the classic nitrile ylide.

Graphical abstract: Synthesis and reactivity of N-heterocyclic carbene (NHC)-supported heavier nitrile ylides

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Article information

Article type
Edge Article
Submitted
30 Nov 2023
Accepted
08 Jan 2024
First published
09 Jan 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 2391-2397

Synthesis and reactivity of N-heterocyclic carbene (NHC)-supported heavier nitrile ylides

D. Sarkar, S. Dutta, F. Hanusch, D. Koley and S. Inoue, Chem. Sci., 2024, 15, 2391 DOI: 10.1039/D3SC06430A

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