(NHCMe)SiCl4: A versatile carbene transfer reagent-synthesis from silicochloroform

Boettcher T, Bassil BS, Zhechkov L, Heine T, Roeschenthaler GV (2013)

Publication Type: Journal article

Publication year: 2013

Journal

Chemical Science Royal Society of Chemistry

Book Volume: 4

Pages Range: 77-83

Journal Issue: 1

DOI: 10.1039/c2sc21214e

Abstract

A new synthetic pathway for the N-heterocyclic carbene adduct (NHC ^Me)SiCl4 (2) (NHC^Me = 1,3-dimethylimidazolidin- 2-ylidene) using silicochloroform is presented. Supported by DFT calculations, the energy for dissociation of 2 into the carbene and the SiCl4 fragment was found to be comparable to carbene transfer reagents based on silver(i) chloride. Compound 2 was used to transfer the NHC ligand to three different phosphorus(iii) chloro compounds, resulting in the neutral complexes (NHC^Me)PCl3 (3a), (NHC^Me)PCl2Ph (3b) and (NHC^Me)PCl2Me (3c). The sterically non-demanding NHC ligand allowed the phosphorus(iii) in complex 3a to be oxidized to phosphorus(v) without loss of the NHC ligand, and afford (NHC^Me)PF4H (4). Furthermore, bis-carbene complexes of Ni(ii) (5) and Pd(ii) (6) were obtained by reacting 2 with the respective metal chlorides. © 2013 The Royal Society of Chemistry.

Involved external institutions

Jacobs University Bremen gGmbH

Germany (DE)

How to cite

APA:

Boettcher, T., Bassil, B.S., Zhechkov, L., Heine, T., & Roeschenthaler, G.-V. (2013). (NHCMe)SiCl4: A versatile carbene transfer reagent-synthesis from silicochloroform. Chemical Science, 4(1), 77-83. https://doi.org/10.1039/c2sc21214e

MLA:

Boettcher, Tobias, et al. "(NHCMe)SiCl4: A versatile carbene transfer reagent-synthesis from silicochloroform." Chemical Science 4.1 (2013): 77-83.

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