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Volumn , Issue 19, 2007, Pages 3050-3054

Reusable scandium/ionic liquid catalyst system for sequential C-C and C-O bond formations between phenols and dienes with atom economy

Author keywords

Annulations; Bicyclic compounds; Heterocycles; Ionic liquids; Scandium

Indexed keywords

2 NAPHTHOL; ALKADIENE; BICYCLO COMPOUND; CHROMAN; DIHYDROBENZOFURAN DERIVATIVE; IONIC LIQUID; ISOPRENE; PHENOL DERIVATIVE; PYRAN DERIVATIVE; SCANDIUM; UNCLASSIFIED DRUG;

EID: 37249088836     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990963     Document Type: Article
Times cited : (7)

References (33)
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    • For one-pot synthesis of dihydrobenzopyrans by the reactions of phenols with dienes using Amberlyst 15 as a reusable catalyst, see: Cichewicz, R. H, Kenyon, V. A, Whitman, S, Morales, N. M, Arguello, J. F, Holman, T. R, Crews, P. J. Am. Chem. Soc. 2004, 126, 14910; and references therein
    • For one-pot synthesis of dihydrobenzopyrans by the reactions of phenols with dienes using Amberlyst 15 as a reusable catalyst, see: Cichewicz, R. H.; Kenyon, V. A.; Whitman, S.; Morales, N. M.; Arguello, J. F.; Holman, T. R.; Crews, P. J. Am. Chem. Soc. 2004, 126, 14910; and references therein.
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    • 3-catalyzed reactions in ionic liquids, see the following. For hydroarylations: (a) Song, C. E.; Jung, D.; Choung, S. Y.; Roh, E. J.; Lee, S. Angew. Chem. Int. Ed. 2004, 43, 6183.
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    • For effects of the anions, see: refs. 9b and 8c and references therein
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    • and ref. 9c. For effects of the alkyl chain lengths of the cations, see
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    • General Procedure for the Sc-IL-Catalyzed Reaction of Phenols and Dienes and Catalyst Recycling: To a solution of phenol and diene (2 equiv) in toluene (0.1 M) and [bmim][PF6, 0.5 equiv) was added Sc(OTf) 3 (20 mol, The resulting mixture was stirred at the reported temperature for 18-48 h. The organic(toluene) layer was decanted to leave the ionic liquid phase containing Sc(OTf)3 which was washed with Et 2O (3 x) for extraction of the product. The combined organic layer was concentrated and the residue was purified by column chromatography on silica gel (EtOAc-n-hexanes, 1:20-1:100) to give the corresponding product. The recovered ionic liquid layer remaining in the vessel was reused without any pre-treatment. For the second cycle, more reactants (phenol and diene) and toluene were added to the recovered ionic liquid layer. 5,7-Dimethoxy-2,2- dimethylchroman (5, Colorless oil EtOAc-n-hexane, 1:20, 1
    • 2: 260.1776; found: 260.1776.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.