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Facile Synthesis of Silver(I)−Carbene Complexes. Useful Carbene Transfer Agents
Abstract
[Ag(Et 2 -Bimy) 2 ][AgBr 2 ] ( 1; Et 2 -Bimy = diethylbenzimidazol-2-ylidene) was obtained readily from the reaction of [Et 2 -BimyH]Br with Ag 2 O. Compound 2, [Ag(Et 2 -Bimy) 2 ]PF 6, was prepared by the reaction of [Et 2 -Bimy]PF 6 with Ag 2 O under basic phase transfer catalysis conditions. Both compounds 1 and 2 are good carbene transfer agents. Thus, Pd(Et 2 -Bimy) 2 Cl 2, Au(Et 2 -Bimy)Br, and [Au(Et 2 -Bimy) 2 ]PF 6 were obtained in high yields using 1 and 2 as carbene sources. The byproduct AgBr or AgCl can be reused to generate 1 under basic phase transfer catalysis conditions. The crystal structure of compound 1 revealed that linear [Ag(Et 2 -Bimy) 2 ] + and [AgBr 2 ] - groups were associated through a short Ag I −Ag I contact (2.956 Å). FAB/mass spectrometry and molar conductivity measurements indicate the existence of ligand-unsupported Ag I −Ag I interactions in the gas phase and acetonitrile solution. 13 C NMR studies suggest that the two Bimy ligands in 1 are fluxional in solution.
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Cited by
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Melaimi, M., Jazzar, R., Soleilhavoup, M., & Bertrand, G. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201702148 · Cited by 788
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Huynh, H. V., Han, Y., Jothibasu, R., & Yang, J. A. (2009) · Organometallics · doi:10.1021/om900667d · Cited by 379
Zhou, H., Zhang, W.-Z., Liu, C.-H., Qu, J.-P., & Lu, X.-B. (2008) · The Journal of Organic Chemistry · doi:10.1021/jo801457r · Cited by 364
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Schaper, L., Hock, S. J., Herrmann, W. A., & Kühn, F. E. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201205119 · Cited by 340
Metal-containing ionic liquids and ionic liquid crystals based on imidazolium moiety
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Metadata
- Authors
- Wang, H. M. J., & Lin, I. J. B.
- Venue
- Organometallics
- Publisher
- American Chemical Society (ACS)
- Published
- 1998-02-12
- Volume
- 17
- Issue
- 5
- Pages
- 972-975
- ISSN
- 0276-7333 (ISSN-L)
- 1520-6041
- OpenAlex
- W1982100202
- Cited by
- 1,172
- References
- 0
- FWCI
- 6.98
- Type
- journal article
- Language
- en
- Open access
- closed
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