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DOI: 10.1055/s-0030-1260322
A Highly Sustainable and Active Catalyst for Suzuki-Miyaura Reaction: Palladium-Supported Ionic Liquid Catalyst (SILC) Coated with Polymer
Publication History
Publication Date:
22 September 2011 (online)
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Abstract
With the aid of an ionic liquid, palladium acetate was immobilized in the pores of silica gel, which was coated with polyethylene terephthalate. The heterogeneous catalyst was effective for Suzuki-Miyaura reactions of ortho-substituted aryl bromides, aryl triflates, and arylboronic acids in aqueous ethanol at room temperature, and could be re-used up to ten times.
Key words
catalysis - green chemistry - heterogeneous catalysis - palladium - supported catalysis
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References and Notes
Coating of Pd-SILC with PET as PET-Pd-SILC (4S): A Pd-SILC (108 mg, 0.027 mmol) silica gel pellet (5 mm in diameter and 5 mm in length) was immersed in a sat. solution of polyethylene terephthalate (60 mg) in 1,1,1,3,3,3-hexafluoro-2-propanol (0.1 mL). After removing the pellet from the solution with tweezers, the pellet was dried overnight in air under ambient conditions. The same procedure was repeated to give PET-Pd-SILC (4S; 123 mg).
14The Suzuki-Miyaura reaction catalyzed by PET-Pd-SILC (4S); synthesis of 4-(2-methyl)phenylacetophenone: K2CO3 (149 mg, 1.08 mmol) and a pellet of PET-Pd-SILC (4S; 123 mg, 0.027 mmol) were added to a solution of 4-bromo-acetophenone (1; 107 mg, 0.54 mmol) and 2-methyl-phenylboronic acid (2; 103 mg, 0.76 mmol) in 50% aq EtOH (2 mL) under nitrogen. The solution was stirred at r.t. for 90 min. After decantation of the organic layer, the SILC pellet was rinsed with an Et2O-EtOH (1:1) mixture. The combined organic layers were evaporated to dryness under reduced pressure. Purification of the residue by column chromatog-raphy (EtOAc-n-hexane, 1:3) provided 4-(2-methyl)-phenylacetophenone (3; 115 mg, 100%).