Advanced search

Coordinatively unsaturated ruthenium complexes as efficient alkyne-azide cycloaddition catalysts

(2012) ORGANOMETALLICS. 31(2). p.756-767
Author
Organization
Abstract
The performance of 16-electron ruthenium complexes with the general formula Cp*Ru(L)X (in which L = phosphine or N-heterocyclic carbene ligand; X = Cl or OCH2CF3) was explored in azide-alkyne cycloaddition reactions that afford the 1,2,3-triazole products. The scope of the Cp*Ru((PPr3)-Pr-i)Cl precatalyst was investigated for terminal alkynes leading to new 1,5-disubstituted 1,2,3-triazoles in high yields. Mechanistic studies were conducted and revealed a number of proposed intermediates. Cp*Ru((PPr3)-Pr-i)(eta(2)-HCCPh)Cl was observed and characterized by H-1, C-13, and P-31 NMR at temperatures between 273 and 213 K. A rare example of N,N-kappa(2)-phosphazide complex, Cp*Ru(kappa(2)-(Pr3PN3Bn)-Pr-i)Cl, was fully characterized, and a single-crystal X-ray diffraction structure was obtained. DFT calculations describe a complete map of the catalytic reactivity with phenylacetylene and/or benzylazide,
Keywords
HETEROCYCLIC CARBENE LIGANDS, TERTIARY PHOSPHINE-LIGANDS, RUCL CP-ASTERISK, 1, 3-DIPOLAR CYCLOADDITION, NUCLEOPHILIC CARBENE, OLEFIN METATHESIS, CLICK CHEMISTRY, STRUCTURAL CHARACTERIZATION, ANTIBACTERIAL ACTIVITY, ETA(5)-C5ME5 MOIETY

Citation

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

Chicago
Lamberti, Marina, George C Fortman, Albert Poater, Julie Broggi, Alexandra MZ Slawin, Luigi Cavallo, and Steven Nolan. 2012. “Coordinatively Unsaturated Ruthenium Complexes as Efficient Alkyne-azide Cycloaddition Catalysts.” Organometallics 31 (2): 756–767.
APA
Lamberti, M., Fortman, G. C., Poater, A., Broggi, J., Slawin, A. M., Cavallo, L., & Nolan, S. (2012). Coordinatively unsaturated ruthenium complexes as efficient alkyne-azide cycloaddition catalysts. ORGANOMETALLICS, 31(2), 756–767.
Vancouver
1.
Lamberti M, Fortman GC, Poater A, Broggi J, Slawin AM, Cavallo L, et al. Coordinatively unsaturated ruthenium complexes as efficient alkyne-azide cycloaddition catalysts. ORGANOMETALLICS. 2012;31(2):756–67.
MLA
Lamberti, Marina et al. “Coordinatively Unsaturated Ruthenium Complexes as Efficient Alkyne-azide Cycloaddition Catalysts.” ORGANOMETALLICS 31.2 (2012): 756–767. Print.
@article{8168913,
  abstract     = {The performance of 16-electron ruthenium complexes with the general formula Cp*Ru(L)X (in which L = phosphine or N-heterocyclic carbene ligand; X = Cl or OCH2CF3) was explored in azide-alkyne cycloaddition reactions that afford the 1,2,3-triazole products. The scope of the Cp*Ru((PPr3)-Pr-i)Cl precatalyst was investigated for terminal alkynes leading to new 1,5-disubstituted 1,2,3-triazoles in high yields. Mechanistic studies were conducted and revealed a number of proposed intermediates. Cp*Ru((PPr3)-Pr-i)(eta(2)-HCCPh)Cl was observed and characterized by H-1, C-13, and P-31 NMR at temperatures between 273 and 213 K. A rare example of N,N-kappa(2)-phosphazide complex, Cp*Ru(kappa(2)-(Pr3PN3Bn)-Pr-i)Cl, was fully characterized, and a single-crystal X-ray diffraction structure was obtained. DFT calculations describe a complete map of the catalytic reactivity with phenylacetylene and/or benzylazide,},
  author       = {Lamberti, Marina and Fortman, George C and Poater, Albert and Broggi, Julie and Slawin, Alexandra MZ and Cavallo, Luigi and Nolan, Steven},
  issn         = {0276-7333},
  journal      = {ORGANOMETALLICS},
  keywords     = {HETEROCYCLIC CARBENE LIGANDS,TERTIARY PHOSPHINE-LIGANDS,RUCL CP-ASTERISK,1,3-DIPOLAR CYCLOADDITION,NUCLEOPHILIC CARBENE,OLEFIN METATHESIS,CLICK CHEMISTRY,STRUCTURAL CHARACTERIZATION,ANTIBACTERIAL ACTIVITY,ETA(5)-C5ME5 MOIETY},
  language     = {eng},
  number       = {2},
  pages        = {756--767},
  title        = {Coordinatively unsaturated ruthenium complexes as efficient alkyne-azide cycloaddition catalysts},
  url          = {http://dx.doi.org/10.1021/om2012425},
  volume       = {31},
  year         = {2012},
}

Altmetric
View in Altmetric
Web of Science
Times cited: