34123-86-9Relevant academic research and scientific papers
Efficient construction of C–C bonds from aryl halides/aryl esters with arylboronic acids catalysed by palladium(II) thiourea complexes
Thimma Sambamoorthy, Manikandan,Rengan, Ramesh,Jan Grzegorz, Malecki
, (2019/11/03)
A new set of palladium(II) complexes comprising phenyl(thiazolyl)thiourea ligands have been successfully synthesized and characterized with the aid of analytical as well as spectral (IR, UV–visible and NMR) methods. A distorted square-planar geometry with N^S coordination mode of thiourea ligands in the new palladium complexes was corroborated by single-crystal X-ray diffraction methods. Interestingly, the palladium(II) thiourea complexes showed the highest catalytic activity with 0.1 mol% catalyst loading in Suzuki–Miyaura cross-coupling reactions utilizing a range of aryl bromides/unactivated aryl chlorides with arylboronic acids as coupling partners in aqueous–organic media. Syntheses of diaryl ketones using aryl esters and arylboronic acids as coupling partners were also achieved with low catalyst loading within 20 h. The potential of our catalyst was demonstrated by its wide substrate scope, low catalyst loadings and high isolated yield. Moreover, the influences of key parameters like solvent, base, temperature and catalyst loading were also investigated.
Highly efficient palladium(II) hydrazone based catalysts for the Suzuki coupling reaction in aqueous medium
Muthumari, Subramanian,Ramesh, Rengan
, p. 52101 - 52112 (2016/06/13)
Synthesis of a new family of air stable palladium(ii)benzhydrazone complexes of the general formula [PdCl(PPh3)(L)] (where HL = thiophene aldehyde benzhydrazones) incorporating PPh3 and chloride as co-ligands has been described through a single and convenient step with good yields. All the new complexes have been fully characterized by means of elemental analysis, IR, UV-vis, and NMR spectral methods. The molecular structures of three of the complexes were determined by single crystal X-ray crystallography, which confirm the coordination mode of benzhydrazone and reveal the presence of a distorted square planar geometry around the Pd ion. The complexes 1-5 (0.05 mol%) have been found to be a highly active catalytic system in the mono and double Suzuki-Miyaura cross coupling reaction of deactivated aryl and heteroaryl bromides with different types of aryl boronic acids in neat water and the maximum yield was up to >99%. Notably, these catalysts work well with ultra-low loading of the catalysts and show high turnover numbers in a short time towards different substrates. Moreover, the catalysts could be simply recovered and reused five times without significant loss of efficiency.
Palladium(ii) thiocarboxamide complexes: Synthesis, characterisation and application to catalytic Suzuki coupling reactions
Sindhuja, Elangovan,Ramesh, Rengan,Liu, Yu
experimental part, p. 5351 - 5361 (2012/05/20)
A simple route to synthesise palladium(ii) complexes from the reaction of N-substituted pyridine-2-thiocarboxamide ligands and PdCl2(PPh 3)2 has been developed. The new complexes are very soluble in common solvents and have been fully characterised (elemental analysis, FT-IR, 1H, 31P, 13C-NMR), including an X-ray diffraction analysis. The molecular structures of all the complexes were determined and reveal the presence of square planar geometry around Pd with little distortion. The complexes were tested in the Suzuki coupling of electronically deactivated aryl and heteroaryl bromides and were found to have much greater activity, without using any promoting additives or phase transfer agent under aerobic conditions. Higher reaction rates are obtained by varying R substituents on the aromatic ring of pyridine-2-thiocarboxamide. The effect of other variables on the cross-coupling reaction, such as temperature, solvent and base, is also reported.
Accelerated luminophore discovery through combinatorial synthesis
Lowry, Michael S.,Hudson, William R.,Pascal Jr., Robert A.,Bernhard, Stefan
, p. 14129 - 14135 (2007/10/03)
A method for accelerating the discovery of ionic luminophores using combinatorial techniques is reported. The photophysical properties of the resulting transition-metal-based chromophores were compared against a series of analogous, traditionally prepared species. The strong overlap between these two sets confirms the identity of the parallel synthesis products and supports the truthfulness of the combinatorial results. Further support for the combinatorial method comes from the adherence of these complexes to the energy gap law. The relationship between the structure of a complex and its photophysical properties was also considered, and static DFT calculations were used to assess whether it is feasible to predict the luminescent behavior of novel materials.
Potent inhibitors of farnesyltransferase and geranylgeranyltransferase-I
Nguyen, Diem N.,Stump, Craig A.,Walsh, Eileen S.,Fernandes, Christine,Davide, Joseph P.,Ellis-Hutchings, Michelle,Robinson, Ronald G.,Williams, Theresa M.,Lobell, Robert B.,Huber, Hans E.,Buser, Carolyn A.
, p. 1269 - 1273 (2007/10/03)
Compound 1 has been shown to be a dual prenylation inhibitor with FPTase (IC50=2 nM) and GGPTase-I (IC50=95 nM). Analogues of 1, which replaced the cyanophenyl group with various biaryls, led to the discovery of highly potent dual FPTase/GGPTase-I inhibitors. 4-Trifluoromethylphenyl, trifluoropentynyl, and trifluoropentyl were identified as good p-cyano replacements.
