Phosphorus derivatives of mesoionic carbenes: synthesis and characterization of triazaphosphole-5-ylidene → BF3 adducts

Trimethylsilyl-substituted triazaphospholes were synthesized by a [3+2] cycloaddition reaction between organic azides and (CH3)3Si–C≡P. In an attempt to isolate their N-alkylated products, the formation of BF3 adducts of unprecedented triazaphosphol-5-ylidenes was found. The nature of the carboncarb...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-08, Vol.59 (68), p.10243-10246
Main Authors: Dettling, Lea, Limberg, Niklas, Küppers, Raphaela, Frost, Daniel, Weber, Manuela, Coles, Nathan T, Andrada, Diego M, Müller, Christian
Format: Article
Language:English
Subjects:
Adducts
Alkylation
Azides (organic)
Bonding strength
Boron
Carbenes
Cycloaddition
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Summary:Trimethylsilyl-substituted triazaphospholes were synthesized by a [3+2] cycloaddition reaction between organic azides and (CH3)3Si–C≡P. In an attempt to isolate their N-alkylated products, the formation of BF3 adducts of unprecedented triazaphosphol-5-ylidenes was found. The nature of the carboncarbene–boron bond was investigated within the DFT framework, revealing a strong donation of electrons from the carbene carbon atom to the boron atom combined with weak back-bonding.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc03268j