123876-56-2Relevant academic research and scientific papers
BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant
Fan, Qing-Hua,Liu, Xintong,Luo, Zhenli,Pan, Yixiao,Xu, Lijin,Yang, Ji,Yao, Zhen,Zhang, Xin
supporting information, p. 5205 - 5211 (2021/07/29)
A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.
Ligand and Cu freeN-arylation of indoles, pyrroles and benzylamines with aryl halides catalyzed by a Pd nanocatalyst
Paul, Abhijit,Chatterjee, Debnath,Banerjee, Srirupa,Yadav, Somnath
supporting information, p. 14447 - 14452 (2020/09/21)
Herein, theN-arylation of aromatic heterocycles like indoles and pyrroles is reported by a Pd nanocatalyst under ligand- and Cu-free conditions. The reaction conditions tolerate several functional groups and work very efficiently for aryl iodides and bromides. Aryl chlorides are also successful as the coupling partners albeit with lower yields. The methodology is also applicable for theN-arylation of aliphatic primary amines as demonstrated by the reactions of benzylamine with several aryl iodides as well as bromides. The recyclable Pd nanocatalyst catalyzes the reaction by a heterogeneous mechanism, which has been demonstrated by several techniques including the three phase test and thein situICP-MS analysis of the reaction mixture.
Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
Kathuria, Lakshay,Samuelson, Ashoka G.
, (2020/06/17)
Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
Design of Hydrazide-Bearing HDACIs Based on Panobinostat and Their p53 and FLT3-ITD Dependency in Antileukemia Activity
Li, Xiaoyang,Jiang, Yuqi,Peterson, Yuri K.,Xu, Tongqiang,Himes, Richard A.,Luo, Xin,Yin, Guilin,Inks, Elizabeth S.,Dolloff, Nathan,Halene, Stephanie,Chan, Sherine S. L.,Chou, C. James
, p. 5501 - 5525 (2020/06/10)
Here, we present a new series of hydrazide-bearing class I selective HDAC inhibitors designed based on panobinostat. The cap, linker, and zinc-binding group were derivatized to improve HDAC affinity and antileukemia efficacy. Lead inhibitor 13a shows picomolar or low nanomolar IC50 values against HDAC1 and HDAC3 and exhibits differential toxicity profiles toward multiple cancer cells with different FLT3 and p53 statuses. 13a indirectly inhibits the FLT3 signaling pathway and down-regulates master antiapoptotic proteins, resulting in the activation of pro-caspase3 in wt-p53 FLT3-ITD MV4-11 cells. While in the wt-FLT3 and p53-null cells, 13a is incapable of causing apoptosis at a therapeutic concentration. The MDM2 antagonist and the proteasome inhibitor promote 13a-triggered apoptosis by preventing p53 degradation. Furthermore, we demonstrate that apoptosis rather than autophagy is the key contributing factor for 13a-triggered cell death. When compared to panobinostat, 13a is not mutagenic and displays superior in vivo bioavailability and a higher AUC0-inf value.
Scalable preparation of stable and reusable silica supported palladium nanoparticles as catalysts for N-alkylation of amines with alcohols
Alshammari, Ahmad S.,Natte, Kishore,Kalevaru, Narayana V.,Bagabas, Abdulaziz,Jagadeesh, Rajenahally V.
, p. 141 - 149 (2020/01/06)
The development of nanoparticles-based heterogeneous catalysts continues to be of scientific and industrial interest for the advancement of sustainable chemical processes. Notably, up-scaling the production of catalysts to sustain unique structural features, activities and selectivities is highly important and remains challenging. Herein, we report the expedient synthesis of Pd-nanoparticles as amination catalysts by the reduction of simple palladium salt on commercial silica using molecular hydrogen. The resulting Pd-nanoparticles constitute stable and reusable catalysts for the synthesis of various N-alkyl amines using borrowing hydrogen technology without the use of any base or additive. By applying this Pd-based catalyst, functionalized and structurally diverse N-alkylated amines as well as some selected drug molecules were synthesized in good to excellent yields. Practical and synthetic utility of this Pd-based amination protocol has been demonstrated by upscaling catalyst preparation and amination reactions to several grams-scales as well as recycling of catalyst. Noteworthy, this Pd-catalyst preparation has been up-scaled to kilogram scale and catalysts prepared in both small (1 g) and large-scale (kg) exhibited similar structural features and activity.
One-pot reductive amination of carbonyl compounds with nitro compounds over a Ni/NiO composite
Hara, Michikazu,Kai, Sayaka,Kamata, Keigo,Kita, Yusuke,Supriadi Rustad, Lesandre Binti
, p. 32296 - 32300 (2020/09/21)
Easily prepared Ni/NiO acts as a heterogeneous catalyst for the one-pot reductive amination of carbonyl compounds with nitroarenes to afford secondary amines with H2as a hydride source. This catalytic system does not require a special technique to avoid air-exposure, in contrast to the common heterogeneous Ni catalysts.
Reduction of Nitroarenes to Anilines with a Benzothiazoline: Application to Enantioselective Synthesis of 2-Arylquinoline Derivatives
Miyagawa, Masamichi,Yamamoto, Ryota,Kobayashi, Nanako,Akiyama, Takahiko
, p. 499 - 502 (2019/02/26)
The metal-free reduction of nitroarenes to aniline derivatives was accomplished in a short time by using a benzothiazoline as the hydrogen donor in combination with a Bronsted acid. An enantioselective synthesis of 2-arylquinolines was achieved by using 1-aryl-3-(2-nitrophenyl)propan-1-ones as starting materials and a combination of a benzothiazoline and a chiral phosphoric acid.
Method for preparing secondary amine compound through imine hydrogenation reduction
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Paragraph 0046-0049, (2019/12/02)
The invention belongs to the technical field of medical and natural compound chemical intermediates and related chemistry, and provides a method for preparing secondary amine compounds through imine hydrogenation reduction. According to the method, the im
Cobalt-Catalyzed Hydrogenations via Olefin Cobaltate and Hydride Intermediates
Sandl, Sebastian,Maier, Thomas M.,Van Leest, Nicolaas P.,Kr?ncke, Susanne,Chakraborty, Uttam,Demeshko, Serhiy,Koszinowski, Konrad,De Bruin, Bas,Meyer, Franc,Bodensteiner, Michael,Herrmann, Carmen,Wolf, Robert,Von Jacobi Wangelin, Axel
, p. 7596 - 7606 (2019/08/20)
Redox noninnocent ligands are a promising tool to moderate electron transfer processes within base-metal catalysts. This report introduces bis(imino)acenaphthene (BIAN) cobaltate complexes as hydrogenation catalysts. Sterically hindered trisubstituted alkenes, imines, and quinolines underwent clean hydrogenation under mild conditions (2-10 bar, 20-80 °C) by use of the stable catalyst precursor [(DippBIAN)CoBr2] and the cocatalyst LiEt3BH. Mechanistic studies support a homogeneous catalysis pathway involving alkene and hydrido cobaltates as active catalyst species. Furthermore, considerable reaction acceleration by alkali cations and Lewis acids was observed. The dinuclear hydridocobaltate anion with bridging hydride ligands was isolated and fully characterized.
Amine-Borane Dehydrogenation and Transfer Hydrogenation Catalyzed by α-Diimine Cobaltates
Maier, Thomas M.,Sandl, Sebastian,Shenderovich, Ilya G.,Jacobi von Wangelin, Axel,Weigand, Jan J.,Wolf, Robert
supporting information, p. 238 - 245 (2019/01/04)
Anionic α-diimine cobalt complexes, such as [K(thf)1.5{(DippBIAN)Co(η4-cod)}] (1; Dipp=2,6-diisopropylphenyl, cod=1,5-cyclooctadiene), catalyze the dehydrogenation of several amine-boranes. Based on the excellent catalytic properties, an especially effective transfer hydrogenation protocol for challenging olefins, imines, and N-heteroarenes was developed. NH3BH3 was used as a dihydrogen surrogate, which transferred up to two equivalents of H2 per NH3BH3. Detailed spectroscopic and mechanistic studies are presented, which document the rate determination by acidic protons in the amine-borane.
