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Volumn 47, Issue 29, 2006, Pages 5083-5087

A rhodium-grafted hydrotalcite as a highly efficient heterogeneous catalyst for 1,4-addition of organoboron reagents to α,β-unsaturated carbonyl compounds

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; CHLORIDE; HYDROTALCITE; MONOMER; NITRILE; ORGANOBORON DERIVATIVE; REAGENT; RHODIUM;

EID: 33744993206     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.075     Document Type: Article
Times cited : (22)

References (39)
  • 28
    • 0035929982 scopus 로고    scopus 로고
    • Friedel-Crafts acylation with organoboron reagents:
    • Friedel-Crafts acylation with organoboron reagents:. Frost C.G., and Wadsworth K.J. Chem. Commun. (2001) 2316
    • (2001) Chem. Commun. , pp. 2316
    • Frost, C.G.1    Wadsworth, K.J.2
  • 29
    • 4644354214 scopus 로고    scopus 로고
    • Phosphinated polystyrene-bound Rh catalyst for 1,4-addition was reported; see:
    • Phosphinated polystyrene-bound Rh catalyst for 1,4-addition was reported; see:. Otomaru Y., Senda T., and Hayashi T. Org. Lett. 6 (2004) 3357
    • (2004) Org. Lett. , vol.6 , pp. 3357
    • Otomaru, Y.1    Senda, T.2    Hayashi, T.3
  • 30
    • 33744990306 scopus 로고    scopus 로고
    • note
    • 2O] was obtained from Tomita Pharmaceutical Co., Ltd.
  • 31
    • 33744979190 scopus 로고    scopus 로고
    • note
    • For recent examples of 1,4-addition reactions using Rh-diene complex catalysts; see Refs. 7c-e.
  • 33
    • 33744967639 scopus 로고    scopus 로고
    • note
    • For the large-scale reaction, 1 (12 mmol), 2 (12 mmol), Rh/HT (0.030 g, Rh: 0.006 mmol), 1,5-cod (0.006 mmol), and 1,4-dioxane (20 mL) were used. The reaction mixture was vigorously stirred at 100 °C under Ar for 12 h. After the reaction, the catalyst was removed by filtration, and the filtrate was evaporated. The crude product was purified by silicagel column chromatography (n-hexane/ethyl acetate, 9:1), thus affording 3 as a colorless oil (81% isolated yield).
  • 34
    • 31444457133 scopus 로고    scopus 로고
    • During the preparation of our manuscript, a high performance homogeneous rhodium catalyst (TOF = 14,000) for the 1,4-addition of arylboroxines to α,β-unsaturated ketones was reported. See:
    • During the preparation of our manuscript, a high performance homogeneous rhodium catalyst (TOF = 14,000) for the 1,4-addition of arylboroxines to α,β-unsaturated ketones was reported. See:. Chen F.-X., Kina A., and Hayashi T. Org. Lett. 8 (2006) 341
    • (2006) Org. Lett. , vol.8 , pp. 341
    • Chen, F.-X.1    Kina, A.2    Hayashi, T.3
  • 35
    • 33744989144 scopus 로고    scopus 로고
    • note
    • In each recycling experiment, 1,5-cod was added.
  • 36
    • 33744967203 scopus 로고    scopus 로고
    • note
    • During adsorption of metal species onto the HT surface, the strong surface basicity of the HT may induce formation of metal hydroxide species; see Refs. 5e,f.
  • 37
    • 33745001936 scopus 로고    scopus 로고
    • note
    • 3-weighted Rh K-edge EXAFS of a recovered Rh/HT after the reaction without 1,5-cod, peaks due to Rh-Rh bonds appeared at around 2.4 Å, which suggested the formation of Rh clusters.
  • 39
    • 33745005850 scopus 로고    scopus 로고
    • note
    • In a three-component reaction, a mixture of benzaldehyde (1 mmol), ethyl cyanoacetate (1 mmol), Rh/HT (0.060 g, Rh: 0.012 mmol), 1,5-cod (0.012 mmol), and 1,4-dioxane (2 mL) was vigorously stirred at 60 °C under Ar for 1 h. Then, 2 (1.5 mmol) was then added to the same flask, and allowed to further react at 100 °C under Ar for 8 h. After the reaction, the catalyst was separated by filtration. The filtrate was evaporated and the crude product was purified by column chromatography using silica (n-hexane/ethyl acetate, 9:1) to afford a pure ethyl 2-cyano-3,3-diphenylpropionate (74% isolated yield).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.