Facile one-step synthesis of bis(NHC) ruthenium benzylidene catalyst for ring-closing metathesis

Zhang, Wenzhen; Bai, Chenxi; Lu, Xiao‐Bing; He, Rong

doi:10.1016/j.jorganchem.2007.04.014

Cited by 26 publications

(11 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Benzylideneruthenium complexes 2 – 5 were prepared in good yield by treating [RuCl 2 (=CHPh)(H 2 IMe)(PPh 3 )] ( 1 )10 with the corresponding pyridine derivative according to the procedure described by Grubbs (Scheme ) 5,6. Complex 1 , which bears a PPh 3 ligand instead of the PCy 3 ligand of the second‐generation Grubbs catalyst, was used in this reaction because dissociation of the PPh 3 ligand in complex 1 proved to be easier than that of PCy 3 in the Grubbs catalyst 11.…”

Section: Resultsmentioning

confidence: 99%

Nitrogen‐Doped Carbon Monolith for Alkaline Supercapacitors and Understanding Nitrogen‐Induced Redox Transitions

Wang

Yin

et al. 2012

Chemistry A European J

379

206

View full text Add to dashboard Cite

A nitrogen-doped porous carbon monolith was synthesized as a pseudo-capacitive electrode for use in alkaline supercapacitors. Ammonia-assisted carbonization was used to dope the surface with nitrogen heteroatoms in a way that replaced carbon atoms but kept the oxygen content constant. Ammonia treatment expanded the micropore size-distributions and increased the specific surface area from 383 m(2) g(-1) to 679 m(2) g(-1). The nitrogen-containing porous carbon material showed a higher capacitance (246 F g(-1)) in comparison with the nitrogen-free one (186 F g(-1)). Ex situ electrochemical spectroscopy was used to investigate the evolution of the nitrogen-containing functional groups on the surface of the N-doped carbon electrodes in a three-electrode cell. In addition, first-principles calculations were explored regarding the electronic structures of different nitrogen groups to determine their relative redox potentials. We proposed possible redox reaction pathways based on the calculated redox affinity of different groups and surface analysis, which involved the reversible attachment/detachment of hydroxy groups between pyridone and pyridine. The oxidation of nitrogen atoms in pyridine was also suggested as a possible reaction pathway.

show abstract

Section: Resultsmentioning

confidence: 99%

Nitrogen‐Doped Carbon Monolith for Alkaline Supercapacitors and Understanding Nitrogen‐Induced Redox Transitions

Wang

Yin

et al. 2012

Chemistry A European J

379

206

View full text Add to dashboard Cite

show abstract

“…8). 61 The use of cyclic alkyl amino carbenes (CAACs), previously reported by Bertrand, 62 as ligands for olefin metathesis catalysts has shown promising results. 63 Both boomerangtype and pyridine-containing ruthenium pre-catalysts were prepared (Fig.…”

Section: Ruthenium-nhc Complexesmentioning

confidence: 99%

N-Heterocyclic carbene-containing complexes in catalysis

Boeda

Nolan

2008

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

View full text Add to dashboard Cite

show abstract

“…The same tendency was observed more recently by Verpoort and co-workers in [(NHC) 2 -RuCl 2 (CHPh)] (NHC = N,N 0 -aryl,alkyl-imidazol-2-ylidene) complexes 7 and Zhang et al for [(NHC) 2 RuCl 2 (CHPh)] (NHC = N,N 0 -diarylimidazol-2-ylidene) complexes. 8 However, Plenio and co-workers recently revealed that introducing an electron-poor NHC in bis-NHC benzylidene-type complexes improved their efficiency in elevated temperature ring-closing metathesis (RCM) reactions. 9 In a follow-up study, they have demonstrated that [(NHC)(NHC ewg )RuCl 2 (CHPh)] complexes, in which NHC ewg is sterically small and was shown to act as the leaving ligand, could be highly efficient in the RCM of hindered substrates.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium Complexes Bearing Two N-Heterocyclic Carbene Ligands in Low Catalyst Loading Olefin Metathesis Reactions

et al. 2010

View full text Add to dashboard Cite

The synthesis of ruthenium indenylidene complexes containing mixed N-heterocyclic carbene ligands featuring one sterically small NHC [IMeMe (1,3,4,5-tetramethylimidazol-2-ylidene), I i PrMe (1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene), and ICy (1,3-dicyclohexylimidazol-2-ylidene)] and one larger congener SIMes (1,3-bis-(2,4,6 trimethylphenyl)imidazolin-2-ylidene) is described. Characterization by X-ray diffraction allowed for calculation of percent buried volume of the small NHCs in these complexes and for speculation on the relationship NHC/catalytic activity. In addition, these complexes displayed an enhanced stability but also a high ability to promote ring-closing metathesis reactions at catalyst loadings as low as 0.05 mol %.

show abstract

Facile one-step synthesis of bis(NHC) ruthenium benzylidene catalyst for ring-closing metathesis

Cited by 26 publications

References 18 publications

Nitrogen‐Doped Carbon Monolith for Alkaline Supercapacitors and Understanding Nitrogen‐Induced Redox Transitions

Nitrogen‐Doped Carbon Monolith for Alkaline Supercapacitors and Understanding Nitrogen‐Induced Redox Transitions

N-Heterocyclic carbene-containing complexes in catalysis

Ruthenium Complexes Bearing Two N-Heterocyclic Carbene Ligands in Low Catalyst Loading Olefin Metathesis Reactions

Contact Info

Product

Resources

About