875274-63-8Relevant academic research and scientific papers
Microwave-assisted and PdII-mediated nitrile-oxime coupling
Garnovskii, Dmitrii A.,Bokach, Nadezhda A.,Pombeiro, Armando J. L.,Haukka, Matti,Frausto Da Silva, Joao J. R.,Kukushkin, Vadim Yu.
, p. 3467 - 3471 (2005)
Refluxing PdCl2 with the ketoximes R1R 2C=NOH (R1R2 = MeMe, MeEt, C5H 10) in RCN (R = Me, Et, nPr, Ph) for 2-3 h results in precipitation of the oxime complexes [PdCl2(R1R2C=NOH) 2], whereas further reflux of the reaction mixture for an additional 6-12 h leads to formation of the chelated species [PdCl2{NH=C(R)ON= CR1R2-κ2N}] (R/R1R2 = Me/MeMe 1; Et/MeMe 2; nPr/MeMe 3; Me/MeEt 4; Me/ C5H10 5; Ph/MeMe 6) by a PdII-mediated coupling between the oximes and the nitriles; complexes 1-6 were isolated in the solid state in 60-75 % yields. The reaction time could be drastically reduced, to 15-30 min, when the system was additionally irradiated with microwaves (100 W, about 60°C). Compounds 1-6 can also be obtained without isolation of the intermediate oxime complexes either by refluxing for 8-15 h or by microwave irradiation (100 W, about 60°C) for 15-30 min. The formulation of 1-6 is based upon satisfactory C, H, and N elemental analyses, FAB mass spectrometry, and IR, 1H and 13C{1H} NMR spectroscopy, while the structures of 1·(Me2CO), 1·(CHCl3), 2·(H 2O), and 6·1/2(H2O) were determined by X-ray single-crystal diffraction. Wiley-VCH Verlag GmbH & Co. KGaA 2005.
