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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.
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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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(e) For C-C bond-forming reactions, see: Gu, Y.; Ogawa, C.; Kobayashi, J.; Mori, Y.; Kobayashi, S. Angew. Chem. Int. Ed. 2006, 45, 7217.
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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
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2: 260.1776; found: 260.1776.
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