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Some recent examples of heterogeneous Pd catalysts fixed on inorganic support for aryl coupling reactions: (a) Ramchandani, R. K.; Uphade, B. S.; Vinod, M. P.; Wakharkar, R. D.; Choudhary, V. R.; Sudalai, A. Chem. Commun. 1997, 2071. (b) Anson, M. S.; Mirza, A. R.; Tonks, L.; Williams, J. M. J. Tetrahedron Lett. 1999, 40, 7147. (c) Mori, K.; Yamaguchi, K.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2002, 124, 11572. (d) Molnar, A.; Papp, A.; Miklos, K.; Forgo, P. Chem. Commun. 2003, 2626. (e) Daku, K. M. L.; Newton, R. F.; Pearce, S. P.; Vile, J.; Williams, J. M. J. Tetrahedron Lett. 2003, 44, 5095. See also earlier references cited in these references.
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3242665412
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note
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2 supported was 560 mg (0.25 mmol/g) based on weight gain.
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0141742644
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3242724284
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note
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2) in n-dodecane (2 mL) were added iodobenzene 1 (112 mg, 1 mmol), cyclohexyl acrylate 2 (189 mL, 1.2 mmol), and tri(n-butyl)amine (279 mL, 2 mmol) under a nitrogen atmosphere. The suspension was heated at 150 °C until disappearance of iodobenzene 1 by GLC monitoring. After being cooled to room temperature, the n-dodecane layer was passed through a silica column with the aid of n-hexane to remove n-dodecane. Subsequently, the product was eluted with n-hexane-ethyl acetate. The n-hexane-ethyl acetate eluent was evaporated to dryness to give a residue that was purified by medium-pressure LC (eluent = ethyl acetate/n-hexane 1:20) to afford cyclohexyl cinnamate 3 (234 mg, 98%). The catalyst was reused intact for the next reaction without any pretreatment.
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