371959-15-8Relevant articles and documents
Versatile and Highly Efficient trans-[Pd(NHC)Cl2(DMS/THT)] Precatalysts for C?N and C?C Coupling Reactions in Green Solvents
Cazin, Catherine S. J.,Liu, Yaxu,Nolan, Steven P.,Peng, Min,Scattolin, Thomas,Van Hecke, Kristof,Voloshkin, Vladislav A.
, (2022/04/20)
A straightforward synthetic procedure to well-defined, air- and moisture- stable trans-[Pd(NHC)Cl2(DMS/THT)] (NHC=IPr, SIPr, IMes, IPrCl, IPr*, IPr#) pre-catalysts is reported. These complexes were obtained by reacting NHC ? HCl imidazolium salts with trans-[PdCl2(DMS/THT)2] precursors with the assistance of the weak base K2CO3 in green acetone at 40 °C. The scalability of this protocol was demonstrated. The catalytic activity of the synthesized complexes was studied in the Buchwald-Hartwig and Suzuki-Miyaura reactions. Remarkably, most of the synthesized complexes exhibit higher catalytic activity with respect to their PEPPSI congeners in the Buchwald-Hartwig amination in 2-MeTHF. In particular, complex trans-[Pd(IPr#)Cl2(DMS)] enabled the coupling of various (hetero)aryl chlorides and primary/secondary amines with a 0.2 mol% catalyst loading. In addition, trans-[Pd(IPr)Cl2(DMS)] showed excellent performance in the room-temperature Suzuki-Miyaura reaction involving various (hetero)aryl chlorides and aryl boronic acids. In summary, the synthesized complexes, especially trans-[Pd(NHC)Cl2(DMS)], can be considered as greener alternatives to classical PEPPSI type catalysts based on the lower toxicity of the throw-away DMS ligand compared to 3-chloropyridine.
Flow synthesis of secondary amines over Ag/Al2O3 catalyst by one-pot reductive amination of aldehydes with nitroarenes
Artiukha, Ekaterina A.,Nuzhdin, Alexey L.,Bukhtiyarova, Galina A.,Bukhtiyarov, Valerii I.
, p. 45856 - 45861 (2017/10/06)
An alumina-supported silver catalyst was investigated in the one-pot reductive amination of aldehydes with nitroarenes in a continuous flow reactor using molecular hydrogen as a reducing agent. A series of secondary amines containing alkyl, OH, OCH3, Cl, Br and CC groups was synthesized in good to excellent yields. The yield of the secondary amine depends on the rate of formation of an intermediate imine. It was shown that the accumulation of carbonaceous deposits on the catalyst is the main reason of catalyst deactivation. The spent catalyst can be easily regenerated and reused without losing catalytic activity.
One-pot reductive amination of aldehydes with nitroarenes over an Au/Al2O3 catalyst in a continuous flow reactor
Artiukha,Nuzhdin,Bukhtiyarova,Zaytsev, S. Yu.,Plyusnin,Shubin, Yu. V.,Bukhtiyarov
, p. 4741 - 4745 (2015/10/05)
One-pot reductive amination of aromatic and aliphatic aldehydes with nitroarenes over an Au/Al2O3 catalyst in a continuous flow reactor using molecular hydrogen as a reducing agent was performed. Various secondary aromatic amines were obtained in good to excellent yields.