Advanced search

Synthesis and characterization of gold(I) complexes of dibenzotropylidene-functionalized NHC ligands (Trop-NHCs)

(2015) ORGANOMETALLICS. 34(1). p.263-274
Author
Organization
Abstract
Gold(I) complexes of dibenzotropylidene-functionalized N-heterocyclic carbene ligands (Trop-NHCs) have been prepared in order to investigate their structural features and to reveal possible interactions of the olefin unit with the metal center. The precursor imidazolium chloride salts (R-1) were generated in a single step using N-substituted imidazoles (R = H, Me, DiPP, Ad) and 1 or 2 equiv of Trop-Cl, generating unsymmetrical and symmetrical NHC-olefin hybrids. The structural parameters of the ligands were determined by synthesis and X-ray diffraction analysis of their corresponding gold(I) chloride complexes, revealing highly flexible steric demands of the Trop unit. Conversion of these complexes with halide-abstracting reagents such as AgNTf2 and NaBArF24 cleanly gave neutral, NTf2-coordinated complexes of the type [(NHC)Au(NTf2)] (R-3) and the cationic bis-NHC-coordinated complexes [(NHC)(2)Au]BArF24 (R-4), respectively. The Gagosz-type complexes R-3 were further tested in the hydration of diphenylacetylene, showing a clear trend in activity depending on the ligands sensitivity to hydrolysis.
Keywords
N-HETEROCYCLIC-CARBENE, CROSS-COUPLING REACTIONS, CATALYSIS, METAL, PHOSPHINE, EFFICIENT, BULKY, HYDROAMINATION, PRECATALYSTS, PARAMETERS

Citation

Please use this url to cite or link to this publication:

Chicago
Brill, Marcel, Alba Collado, David B Cordes, Alexandra MZ Slawin, Matthias Vogt, Hansjoerg Gruetzmacher, and Steven Nolan. 2015. “Synthesis and Characterization of gold(I) Complexes of Dibenzotropylidene-functionalized NHC Ligands (Trop-NHCs).” Organometallics 34 (1): 263–274.
APA
Brill, M., Collado, A., Cordes, D. B., Slawin, A. M., Vogt, M., Gruetzmacher, H., & Nolan, S. (2015). Synthesis and characterization of gold(I) complexes of dibenzotropylidene-functionalized NHC ligands (Trop-NHCs). ORGANOMETALLICS, 34(1), 263–274.
Vancouver
1.
Brill M, Collado A, Cordes DB, Slawin AM, Vogt M, Gruetzmacher H, et al. Synthesis and characterization of gold(I) complexes of dibenzotropylidene-functionalized NHC ligands (Trop-NHCs). ORGANOMETALLICS. 2015;34(1):263–74.
MLA
Brill, Marcel, Alba Collado, David B Cordes, et al. “Synthesis and Characterization of gold(I) Complexes of Dibenzotropylidene-functionalized NHC Ligands (Trop-NHCs).” ORGANOMETALLICS 34.1 (2015): 263–274. Print.
@article{8168362,
  abstract     = {Gold(I) complexes of dibenzotropylidene-functionalized N-heterocyclic carbene ligands (Trop-NHCs) have been prepared in order to investigate their structural features and to reveal possible interactions of the olefin unit with the metal center. The precursor imidazolium chloride salts (R-1) were generated in a single step using N-substituted imidazoles (R = H, Me, DiPP, Ad) and 1 or 2 equiv of Trop-Cl, generating unsymmetrical and symmetrical NHC-olefin hybrids. The structural parameters of the ligands were determined by synthesis and X-ray diffraction analysis of their corresponding gold(I) chloride complexes, revealing highly flexible steric demands of the Trop unit. Conversion of these complexes with halide-abstracting reagents such as AgNTf2 and NaBArF24 cleanly gave neutral, NTf2-coordinated complexes of the type [(NHC)Au(NTf2)] (R-3) and the cationic bis-NHC-coordinated complexes [(NHC)(2)Au]BArF24 (R-4), respectively. The Gagosz-type complexes R-3 were further tested in the hydration of diphenylacetylene, showing a clear trend in activity depending on the ligands sensitivity to hydrolysis.},
  author       = {Brill, Marcel and Collado, Alba and Cordes, David B and Slawin, Alexandra MZ and Vogt, Matthias and Gruetzmacher, Hansjoerg and Nolan, Steven},
  issn         = {0276-7333},
  journal      = {ORGANOMETALLICS},
  language     = {eng},
  number       = {1},
  pages        = {263--274},
  title        = {Synthesis and characterization of gold(I) complexes of dibenzotropylidene-functionalized NHC ligands (Trop-NHCs)},
  url          = {http://dx.doi.org/10.1021/om501093s},
  volume       = {34},
  year         = {2015},
}

Altmetric
View in Altmetric
Web of Science
Times cited: