Palladium(II) complexes bearing the new pincer ligand 3,5-bis(indazol-2- ylmethyl)toluene; Synthesis and catalytic properties

Inorganic Chemistry Communications

Volumn 13, Issue 9, 2010, Pages 1025-1028

  Hurtado, John ^a   Ibañez, Andrés ^b   Rojas, René ^a,b   Valderrama, Mauricio ^a  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

^b CIMAT   (Chile)

Author keywords

Catalytic activity; Cyclometalated complexes; Palladium; Pincer ligand

Indexed keywords

EID: 77955425187     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2010.06.001     Document Type: Article

References (44)

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32. 13C). Mass spectra were obtained on a Micromass Quattro LC-Z electrospray mass spectrometer. Melting points were determined using an Electrothermal melting point apparatus in open capillary tubes and are uncorrected.
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35. - 3, respectively.
36. 2), 119.3 (C8,8′), 120.1 (C11,11′), 122.1 (C1), 122.1 (C4), 123.4 (C10,10′), 125.7 (C7,7′), 128.2 (C9,9′), 126.8 (C2,C6), 134.5 (C13,13′), 136.1 (C3,C5) and 149.8 (C 12,12′) ppm.
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38. - 1): ν 1630 s, 1521 s, 1435 s, 1376 m, 1317 s, 1167 m, 1142 s, 759 s, 361 m.
39. The polymerization was carried out by charging a 30 mL Parr stainless steel autoclave (in a glovebox under an inert nitrogen atmosphere) with toluene and the desired amount of cocatalyst (MAO/toluene 10%) and complex 2 dissolved in a minimum amount of dichloromethane. The autoclave was sealed, brought out of the glovebox and connected to a mechanical stirrer, a temperature controller and an ethylene consumption control. The reaction was ended by the addition of HCl-methanol (20% v/v). The polymer was isolated by filtration, washed with acetone and dried overnight at room temperature. The polymers were characterized by infrared spectroscopy (FTIR), gel permeation chromatography (GPC) and differential scanning chromatography (DSC). Molar mass distribution was obtained with Waters (Alliance GPC 2000) high-temperature GPC instrument equipped with three Styragel HT type columns (HT3, HT5 and HT6E). 1,2,4-Trichlorobenzene was used as solvent, at a flow rate of 1 mL/min and a temperature of 135 °C. The columns were calibrated with polystyrene standards. Polymer melting points (Tm) were determined by differential scanning calorimetry using DSC 2920 TA Instrument equipment. Heating scans at 10 °C/min from - 10 °C to 170 °C. Reported results are those obtained in the second scan.
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42. The Suzuki coupling reactions were carried out in a microwave tube in the presence of air. The reaction mixture was irradiated on a CEM Discover mono-mode microwave apparatus for 40 min. The mixture was cooled and volatiles were removed under vacuum. The formed product was extracted with petroleum ether and purified by tin layer chromatography on silicagel. NMR was used to check the purity of the compounds and the yield is based on aryl bromide.
43. Heck reactions were performed in a microwave tube. Palladium complex (1% mmol), triethylamine (0.42 mL; 3.0 mmol), iodobenzene (2.0 mmol) methyl acrylate (0.27 mL; 3.0 mmol) and dimethylformamide (10 mL) were added and the resulting mixture was microwave irradiated (40 min, 150 °C, 150 W). The resulting product was isolated by extractive workup with dichloromethane followed by flash column chromatography on silica gel (eluted with hexane/diethyl ether 12/1). NMR was used to check the products.
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