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 language | English |
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Pages (from-to) | 23476-23479 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 59 |
Issue number | 52 |
DOIs | |
State | Published - 21 Dec 2020 |
Externally published | Yes |
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.
Funders | Funder number |
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Israel Ministry of Science Technology & Space | |
Israeli Science Foundation | |
Ministry of Science, Technology and Space | 65692 |
Israel Science Foundation | 1449/19 |
Keywords
- N-based Lewis acids
- frustrated Lewis pairs
- metal-free bond activation
- nitrenium
- silanes