Issue 28, 2023

Anionic N-heterocyclic carbenes featuring weakly coordinating perfluoroalkylphosphorane moieties

Abstract

The anionic 1-methyl-3-(tris(pentafluoroethyl)difluorophosphorane)imidazoline-2-ylidenate 3 and the 1,3-bis(tris(pentafluoroethyl)difluorophosphorane)imidazoline-2-ylidenate dianion 4 were obtained in high yield by deprotonation of {(C2F5)3PF2}-methylimidazole 1 and the {(C2F5)3PF2}2-imidazolate anion 2. Carbenes 3 and 4 are first examples for a novel class of NHCs carrying weakly coordinating anions (WCA-NHCs). First reactions of these new ligands with elemental selenium and chloro(phosphine)gold(I) complexes to result in an anionic selenium adduct (5) and WCA-NHC gold complexes (6 and 7) have been undertaken. The structural and spectroscopic properties of these NHC derivatives in conjunction with data from quantum chemical calculations provide an insight into the electronic and steric properties of the WCA-NHCs 3 and 4. Especially the combination of properties such as weakly coordinating periphery combined with the coordinative carbene center, negative charge, large buried volume (%Vbur), and strong σ-donor as well as efficient π-acceptor ability render NHCs 3 and 4 unique and promising new ligands.

Graphical abstract: Anionic N-heterocyclic carbenes featuring weakly coordinating perfluoroalkylphosphorane moieties

Supplementary files

Article information

Article type
Paper
Submitted
26 апр 2023
Accepted
12 май 2023
First published
15 май 2023

Dalton Trans., 2023,52, 9553-9561

Anionic N-heterocyclic carbenes featuring weakly coordinating perfluoroalkylphosphorane moieties

L. Zapf, U. Radius and M. Finze, Dalton Trans., 2023, 52, 9553 DOI: 10.1039/D3DT01249B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements