We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Tricyanoborane‐Functionalized Anionic N‐Heterocyclic Carbenes: Adjustment of Charge and Stereo‐Electronic Properties.
- Authors
Zapf, Ludwig; Peters, Sven; Bertermann, Rüdiger; Radius, Udo; Finze, Maik
- Abstract
The 1‐methyl‐3‐(tricyanoborane)imidazolin‐2‐ylidenate anion (2) was obtained in high yield by deprotonation of the B(CN)3‐methylimidazole adduct 1. Regarding charge and stereo‐electronic properties, anion 2 closes the gap between well‐known neutral NHCs and the ditopic dianionic NHC, the 1,3‐bis(tricyanoborane)imidazolin‐2‐ylidenate dianion (IIb). The influence of the number of N‐bonded tricyanoborane moieties on the σ‐donating and π‐accepting properties of NHCs was assessed by quantum chemical calculations and verified by experimental data on 2, IIb, and 1,3‐dimethylimidazolin‐2‐ylidene (IMe, IIa). Therefore NHC 2, which acts as a ditopic ligand via the carbene center and the cyano groups, was reacted with alkyl iodides, selenium, and [Ni(CO)4] yielding alkylated imidazoles 3 and 4, the anionic selenium adduct 5, and the anionic nickel tricarbonyl complex 8, respectively. The results of this study prove that charge, number of coordination sites, buried volume (%Vbur) and σ‐donor and π‐acceptor abilities of NHCs can be effectively fine‐tuned via the number of tricyanoborane substituents.
- Subjects
CYANO group; CARBENES; ALKYL iodide; DIANIONS; SELENIUM; IMIDAZOLES; CARBENE synthesis
- Publication
Chemistry - A European Journal, 2022, Vol 28, Issue 39, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202200275