25287-28-9Relevant academic research and scientific papers
Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines
Kathuria, Lakshay,Samuelson, Ashoka G.
, (2020/12/28)
Enantioselective reduction of imines to the corresponding chiral secondary amines has been studied using a series of chiral half-sandwich iridium complexes. Chiral N-heterocyclic carbene (NHC) ligands in these complexes were synthesized from readily available, naturally occurring amino acids. Inexpensive phenylsilane was used as a convenient hydrogen donor. Under the optimized conditions, Ir-NHC complexes could reduce ketimines in good yields, albeit with moderate enantiomeric excess (ee). The phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands.
Construction of Stable Metal–Organic Framework Platforms Embedding N-Heterocyclic Carbene Metal Complexes for Selective Catalysis
Kim, Hyunyong,Kim, Hyunseok,Kim, Kimoon,Lee, Eunsung
supporting information, p. 18687 - 18697 (2021/12/17)
We report a bottom-up approach to immobilize catalysts into MOFs, including copper halides and gold chloride in a predictable manner. Interestingly, the structures of MOFs bearing NHC metal complexes maintained a similar 4-fold interpenetrated cube. They
Cu/Ni-doped sulfated zirconium oxide immobilized on CdFe2O4 NPs: a cheap, sustainable and magnetically recyclable inorgano-catalyst for the efficient preparation of α-aminonitriles in aqueous media
Nasseri, Mohammad Ali,Ramezani-Moghadam, Simin,Kazemnejadi, Milad,Allahresani, Ali
, p. 4233 - 4256 (2020/07/08)
Abstract: A new multifunctional bimetallic nanocatalyst was prepared by immobilization of Cu/Ni-doped sulfated zirconium oxide on magnetic cadmium ferrite (CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni) and used as an efficient recyclable catalyst for one-pot as well as stepwise preparation of α-aminonitriles under mild conditions. The magnetic nanocatalyst was characterized by FTIR, TGA, VSM, XRD, EDX, FE-SEM, and TEM analyses. Also, the surface acidity of the catalyst was measured by pyridine adsorption assay. The catalyst possesses various active sites which could catalyst a variety of aromatic and aliphatic aldehydes to the corresponding α-amionitriles under moderate to high yields in the presence of aniline. Furthermore, transformation of ketones to the desired α-amionitriles and some bis-aminonitriles was also performed by this method. The catalyst could be readily recovered from the reaction mixture and reused for several times without significant loss of activity. Graphic abstract: A general and efficient method has been developed for transformation of a variety of aliphatic, aromatic aldehydes and ketones to the corresponding α-aminonitriles using a multifunctional recyclable CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni nanocatalyst.[Figure not available: see fulltext.]
Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
Virant, Miha,Mihela?, Mateja,Gazvoda, Martin,Cotman, Andrej E.,Frantar, Anja,Pinter, Balazs,Ko?mrlj, Janez
supporting information, p. 2157 - 2161 (2020/02/13)
The cationic palladium(II) complex 1 of pyridyl-mesoionic carbene ligand catalyzes Markovnikov-selective intermolecular hydroamination between anilines and terminal alkynes into the corresponding imines. The reaction proceeds at room temperature, in the a
Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles
Pantaine, Lo?c R.E.,Milligan, John A.,Matsui, Jennifer K.,Kelly, Christopher B.,Molander, Gary A.
supporting information, p. 2317 - 2321 (2019/03/26)
Photoredox-mediated radical/polar crossover (RPC) processes offer new avenues for the synthesis of cyclic molecules. This process has been realized for the construction of medium-sized saturated nitrogen heterocycles. Photocatalytically generated alkyl ra
Rhodium-Catalyzed C=N Bond Formation through a Rebound Hydrolysis Mechanism and Application in β-Lactam Synthesis
Chen, Long,Zhang, Linxing,Shao, Ying,Xu, Guangyang,Zhang, Xinhao,Tang, Shengbiao,Sun, Jiangtao
supporting information, p. 4124 - 4127 (2019/06/08)
A rhodium-catalyzed reaction of N-hydroxyanilines with diazo compounds to produce α-imino esters was developed. Distinct from the commonly accepted 1,2-H transfer for normal X-H insertion reactions, density functional theory calculations indicate that this transformation proceeds via a novel rebound hydrolysis mechanism. Furthermore, a three-component reaction was explored to synthesize highly functionalized β-lactams in good yields and diastereoselectivities.
P-Stereogenic and Non-P-Stereogenic Ir-MaxPHOX in the Asymmetric Hydrogenation of N -Aryl Imines. Isolation and X-ray Analysis of Imine Iridacycles
Salomó, Ernest,Rojo, Pep,Hernández-Lladó, Pol,Riera, Antoni,Verdaguer, Xavier
, p. 4618 - 4627 (2018/04/26)
A small library of Ir-MaxPHOX catalysts has been applied to the asymmetric hydrogenation of N-aryl imines. A structure-activity analysis of the three-chiral-center MaxPHOX ligand has been performed. Using complex 1b, the hydrogenation of N-aryl imines too
An efficient proline-based homogeneous organocatalyst with recyclability
Li, Qiang,Li, Yuan,Wang, Jingdong,Lin, Yingjie,Wei, Zhonglin,Duan, Haifeng,Yang, Qingbiao,Bai, Fuquan,Li, Yaoxian
supporting information, p. 827 - 831 (2018/02/03)
In this work, a homogeneous organocatalyst was developed for the asymmetric reduction of imines. This catalyst could be separated by cyclodextrin-modified Fe3O4@SiO2 magnetic nanoparticles and then released back into a fre
Thiolate-Protected Au 25 (SC 2 H 4 Ph) 18 Nanoclusters as a Catalyst for Intermolecular Hydroamination of Terminal Alkynes
Nagata, Tatsuki,Adachi, Yurina,Obora, Yasushi
, p. 2655 - 2659 (2018/12/14)
Au 25 (SC 2 H 4 Ph) 18 nanoclusters have high catalytic activity for hydroamination of terminal alkynes. This reaction proceeds under O 2 or air. The presence of molecular oxygen has a profound effect
A green and efficient hydration of alkynes catalyzed by hierarchically porous poly(ionic liquid)s solid strong acids
Tao, Duan-Jian,Liu, Fujian,Wang, Lin,Jiang, Lilong
, p. 56 - 63 (2018/07/29)
The catalytic conversion of alkynes into ketones via hydration has received considerable attention, because the ketones are very important intermediates in the chemical and pharmaceutical industries. The hydration of alkynes was usually performed with rather complicated processes in presence of liquid acids or highly toxic metal catalysts. We report here a novel metal free and efficient route to conversion of alkynes into ketones catalyzed by hierarchically porous poly(ionic liquid)s solid strong acids, which were synthesized from one-step, template-free copolymerization of divinylbenzene (DVB) with nitrogen containing monomers under solvothermal condition, further by post grafting with strong acid ionic liquid groups. The porous poly(ionic liquid)s solid acids have large BET surface areas, hierarchical nanopores and enhanced acid strength. A variety of alkynes could be effectively transformed into ketones catalyzed by the synthesized porous poly(ionic liquid)s solid acids under green and mild conditions, which were much better than those of Amberlyst 15, phosphotungstic acid and sulfuric acid. Furthermore, the porous poly(ionic liquid)s solid acids also show excellent activities and good reusability in direct hydroamination of amines with phenylacetylene. This work largely expands the wide applications of porous poly(ionic liquid)s solid strong acids in hydration and hydroamination, which develops a green, efficient and cost effective approach for conversion of low cost alkynes into high-value added ketones.
