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An industrially viable catalyst system for palladium-catalyzed telomerizations of 1,3-butadiene with alcohols

(2004) CHEMISTRY-A EUROPEAN JOURNAL. 10(16). p.3891-3900
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Abstract
The telomerization reaction of 1,3-butadiene with alcohols to give alkyl octadienyl ethers in the presence of palladium-carbene catalysts has been studied in detail. Unprecedented catalyst efficiency with turnover numbers (TON) up to 1500000 and turnover frequencies (TOF) up to 100000h(-1) have been obtained after optimization for the reaction of methanol in the presence of an excess of in situ generated carbene ligands. High yields (75-97%) and catalyst productivities (TON 15000-100000) are observed for other aliphatic alcohols and phenols. For comparison five carbene-palladium(0) complexes have been synthesized and characterized by X-ray crystallography. Both electronic and steric effects on the stability and reactivity of the catalysts have been discussed on the basis of density functional theory calculations.
Keywords
butadiene, carbene, homogeneous catalysis, palladium, telomerization, N-HETEROCYCLIC CARBENE, TEMPERATURE IONIC LIQUIDS, ARYL CHLORIDES, METAL-COMPLEXES, (ETA-1, ETA-3-OCTADIENEDIYL)PALLADIUM COMPLEXES, BIPHASIC TELOMERIZATION, DIENE OLIGOMERIZATION, NUCLEOPHILIC-ADDITION, COUPLING REACTIONS, FINE CHEMICALS

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Chicago
Jackstell, R, S Harkal, HJ Jiao, A Spannenberg, C Borgmann, D Rottger, F Nierlich, et al. 2004. “An Industrially Viable Catalyst System for Palladium-catalyzed Telomerizations of 1,3-butadiene with Alcohols.” Chemistry-a European Journal 10 (16): 3891–3900.
APA
Jackstell, R., Harkal, S., Jiao, H., Spannenberg, A., Borgmann, C., Rottger, D., Nierlich, F., et al. (2004). An industrially viable catalyst system for palladium-catalyzed telomerizations of 1,3-butadiene with alcohols. CHEMISTRY-A EUROPEAN JOURNAL, 10(16), 3891–3900.
Vancouver
1.
Jackstell R, Harkal S, Jiao H, Spannenberg A, Borgmann C, Rottger D, et al. An industrially viable catalyst system for palladium-catalyzed telomerizations of 1,3-butadiene with alcohols. CHEMISTRY-A EUROPEAN JOURNAL. 2004;10(16):3891–900.
MLA
Jackstell, R, S Harkal, HJ Jiao, et al. “An Industrially Viable Catalyst System for Palladium-catalyzed Telomerizations of 1,3-butadiene with Alcohols.” CHEMISTRY-A EUROPEAN JOURNAL 10.16 (2004): 3891–3900. Print.
@article{8170242,
  abstract     = {The telomerization reaction of 1,3-butadiene with alcohols to give alkyl octadienyl ethers in the presence of palladium-carbene catalysts has been studied in detail. Unprecedented catalyst efficiency with turnover numbers (TON) up to 1500000 and turnover frequencies (TOF) up to 100000h(-1) have been obtained after optimization for the reaction of methanol in the presence of an excess of in situ generated carbene ligands. High yields (75-97\%) and catalyst productivities (TON 15000-100000) are observed for other aliphatic alcohols and phenols. For comparison five carbene-palladium(0) complexes have been synthesized and characterized by X-ray crystallography. Both electronic and steric effects on the stability and reactivity of the catalysts have been discussed on the basis of density functional theory calculations.},
  author       = {Jackstell, R and Harkal, S and Jiao, HJ and Spannenberg, A and Borgmann, C and Rottger, D and Nierlich, F and Elliot, M and Niven, S and Cavell, KJ and Navarro, O and Viciu, MS and Nolan, Steven and Beller, M},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keyword      = {butadiene,carbene,homogeneous catalysis,palladium,telomerization,N-HETEROCYCLIC CARBENE,TEMPERATURE IONIC LIQUIDS,ARYL CHLORIDES,METAL-COMPLEXES,(ETA-1,ETA-3-OCTADIENEDIYL)PALLADIUM COMPLEXES,BIPHASIC TELOMERIZATION,DIENE OLIGOMERIZATION,NUCLEOPHILIC-ADDITION,COUPLING REACTIONS,FINE CHEMICALS},
  language     = {eng},
  number       = {16},
  pages        = {3891--3900},
  title        = {An industrially viable catalyst system for palladium-catalyzed telomerizations of 1,3-butadiene with alcohols},
  url          = {http://dx.doi.org/10.1002/chem.200400182},
  volume       = {10},
  year         = {2004},
}

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