Preparation of polymer-supported palladium/N-heterocyclic carbene complex for Suzuki cross-coupling reactions

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1837-1840

  Byun, Jang Woong ^a   Lee, Yoon Sik ^a  

^a Seoul National University   (South Korea)

Author keywords

Heterogeneous catalysis; Palladium (Pd); Polymer supported N heterocyclic carbene (NHC); Suzuki cross coupling

Indexed keywords

BENZENEBORONIC ACID; CARBENOID; HALIDE; HETEROCYCLIC COMPOUND; LIGAND; PALLADIUM; POLYMER; POLYSTYRENE DERIVATIVE; RESIN;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; SUZUKI REACTION;

LATEOLABRAX JAPONICUS;

EID: 1242271378     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.021     Document Type: Article

References (21)

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16. A typical procedure for the preparation of an imidazolium-loaded polymeric support ( 1 ). The imidazolium-loaded polymeric support ( 1 ) was prepared from commercially available chloromethyl polystyrene (CM PS) resin cross-linked with 1% DVB (100-200 mesh, BeadTech Inc.). A mixture of CM PS resin (1.0 g, 2.3 mmol Cl/g polymeric support) and 1-methylimidazole (1.8 mL, 23.0 mmol) in NMP (100 mL) was slowly agitated at 80°C for 12 h. After cooling to room temperature, the reaction mixture was filtered, and the polymeric support was washed with NMP (20 mL × 3), 0.1 N aq HCl (20 mL × 3), and methanol (20 mL × 3), followed by drying under reduced pressure to give 1 . The loading of the imidazolium groups was determined by means of the nitrogen content obtained from elementary analysis.
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19. A typical procedure for measuring the swelling properties of the imidazolium-loaded polymeric supports ( 1 ). The swelling volumes of the imidazolium-loaded polymeric support in various solvents were measured in a fritted column (ID 0.8 cm, length 20 cm). The polymeric support (1.0 g) was swollen in a solvent at room temperature for 30 min, and then washed with a 10-fold volume of each solvent. After filtering out the solvent, the volume of the polymeric support was measured.
20. 3 (106 mg, 1.0 mmol). The mixture was sonicated at room temperature for 30 min, and then agitated for 2 h at 50°C in a shaking incubator. After filtration, the polymeric support was washed vigorously with distilled water (10 mL × 5), MeOH (10 mL × 5), and dried under reduced pressure to give 2 . To measure the amount of Pd loaded on the polymeric support, the polymeric support (10 mg) was treated with a mixture (5 mL) of hydrochloric acid and nitric acid (1:1, v/v) at room temperature for 30 min. After the orange-colored solution was filtered, the polymeric support was washed with distilled water (2.5 mL × 2), and then, the filtrate and the washing solution were combined to determine the amount of Pd by inductively coupled plasma-atomic emission spectrometry (ICP-AES).
21. 4 followed by evaporation under reduced pressure, the conversion of the starting iodobenzene was determined by GC-MS analysis with an appropriate internal standard (anisole). The chemical identification of the product was performed by GC-MS from the mass database library (WILEY 275), showing good similarity (>95%) with authentic data. After the biphenyl product was isolated by column chromatography (eluent; n-hexane), the isolation yield was calculated from the mass of the product (71. 9 mg, 93.3% yield), and the purity of the isolated product was determined by GC analysis (99.5% GC purity).