Frustrated Lewis Pairs Comprising Nitrogen Lewis Acids for Si–H Bond Activation

Idan Avigdori, Alla Pogoreltsev, Alexander Kaushanski, Natalia Fridman, Mark Gandelman

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

N-heterocyclic nitrogen Lewis acids are a recent addition to the field of organic chemistry. Based on nitrenium cations, these acids where previously shown to generate Lewis adducts when combined with the appropriate Lewis bases. Herein, a triazinium-based Lewis acid was combined with tBu3P to generate a frustrated Lewis pair (FLP) capable of cleaving, for the first time, Si−H bonds in silanes. Whereas low yields were initially encountered owing to insufficient Lewis acidity, a new nitrenium-based Lewis acid was synthesized, and its superior Lewis acidity was experimentally and computationally confirmed. A FLP based on this acid cleaved the Si−H bond in PhSiH3, generating the triazane product in a quantitative yield. This unprecedented N−H triazane was fully characterized by multinuclear NMR techniques and single-crystal X-ray crystallography. A new class of compounds, N-H triazanes display the potential capacity to participate in hydride transfer reactions.

Original languageEnglish
Pages (from-to)23476-23479
Number of pages4
JournalAngewandte Chemie - International Edition
Volume59
Issue number52
DOIs
StatePublished - 21 Dec 2020
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

Funding

This work was supported by the Israel Ministry of Science Technology & Space, Grant 65692, and the Israeli Science Foundation, Grant 1449/19. This work was supported by the Israel Ministry of Science Technology & Space, Grant 65692, and the Israeli Science Foundation, Grant 1449/19.

FundersFunder number
Israel Ministry of Science Technology & Space
Israeli Science Foundation
Ministry of Science, Technology and Space65692
Israel Science Foundation1449/19

    Keywords

    • N-based Lewis acids
    • frustrated Lewis pairs
    • metal-free bond activation
    • nitrenium
    • silanes

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