1621393-73-4Relevant articles and documents
Cross-coupling reactions in water using ionic liquid-based palladium(II)-phosphinite complexes as outstanding catalysts
Meric, Nermin,Aydemir, Murat,Iik, Uur,Ocak, Yusuf Selim,Rafikova, Khadichakhan,Paa, Salih,Kayan, Cezmi,Durap, Feyyaz,Zazybin, Alexey,Temel, Hamdi
, p. 818 - 825 (2014)
Two new phosphinite ligands based on ionic liquids [(Ph2PO)C7H14N2Cl]Cl (1) and [(Cy2PO)C7H14N2Cl]Cl (2) were synthesized by reaction of 1-(3-chloro-2-hydoxypropyl)-3-methylimidazolium chloride, [C7H15N2OCl]Cl, with one equivalent of chlorodiphenylphosphine or chlorodicyclohexylphosphine, respectively, in anhydrous CH2Cl2 and under argon atmosphere. The reactions of 1 and 2 with MCl2(cod) (M=Pd, Pt; cod = 1,5-cyclooctadiene) yield complexes cis-[M([(Ph2PO)C7H14N2Cl]Cl)2Cl2] and cis-[M(Cy2PO) C7H14N2Cl]Cl)2Cl2], respectively. All complexes were isolated as analytically pure substances and characterized using multinuclear. NMR and infrared spectroscopies and elemental analysis. The catalytic activity of palladium complexes based on ionic liquid phosphinite ligands 1 and 2 was investigated in Suzuki cross-coupling. They show outstanding catalytic activity in coupling of a series of aryl bromides or aryl iodides with phenylboronic acid under the optimized reaction conditions in water. The complexes provide turnover frequencies of 57 600 and 232 800 h-1 in Suzuki coupling reactions of phenylboronic acid with p-bromoacetophenone or p-iodoacetophenone, respectively, which are the highest values ever reported among similar complexes for Suzuki coupling reactions in water as sole solvent in homogeneous catalysis. Furthermore, the palladium complexes were also found to be highly active catalysts in the Heck reaction affording trans-stilbenes.
Ionic liquid based Ru(II)-phosphinite compounds and their catalytic use in transfer hydrogenation: X-ray structure of an ionic compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol
Aydemir, Murat,Rafikova, Khadichakhan,Kystaubayeva, Nurzhamal,Pa?a, Salih,Meri?, Nermin,Ocak, Yusuf Selim,Zazybin, Alexey,Temel, Hamdi,Gürbüz, Nevin,?zdemir, Ismail
, p. 245 - 255 (2014/07/21)
The compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol chloride (1) was prepared from the reaction of 1-methylimidazole with epichlorohydrine. The corresponding phosphinite ligands were synthesized by the reaction 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol chloride, [C7H 15N2OCl]Cl with one equivalent of chlorodiphenylphosphine or chlorodicyclohexylphosphine, in anhydrous CH2Cl2 and under an inert argon atmosphere. [Ru(η6-arene)(μ-Cl)Cl] 2 dimers readily react with the phosphinite ligands [(Ph 2PO)-C7H14N2Cl]Cl (2) or [(Cy 2PO)-C7H14N2Cl]Cl (3) at room temperature to afford the cationic derivatives [Ru((Ph2PO)-C 7H14N2Cl)(η6-arene)Cl 2]Cl and [Ru((Cy2PO)-C7H14N 2Cl)(η6-arene)Cl2]Cl {arene: benzene (4), (5); p-cymene (6), (7)}. The structures of these ligands and their corresponding complexes have been elucidated by a combination of multinuclear NMR and IR spectroscopy, TGA/DTA and elemental analysis. The molecular structure of the ionic compound 1 was also determined by an X-ray single crystal diffraction study. Furthermore, the catalytic activity of complexes 4-7 for the transfer hydrogenation of various ketones was investigated and these complexes were found to be efficient catalysts in the transfer hydrogenation of various ketones, with excellent conversions up to 99%. Specifically, [Ru((Cy2PO)- C7H14N2Cl)(η6-benzene)Cl 2]Cl (5) and [Ru((Cy2PO)-C7H14N 2Cl)(η6-p-cymene)Cl2]Cl (7) act as excellent catalysts, giving the corresponding alcohols in 98-99% conversions in 5 min (TOF ≤ 1188 h-1).
