13159-74-5Relevant academic research and scientific papers
Zinc-catalyzed reduction of imines by triethylsilane
Kumar, K. Anil,Sreelekha,Shivakumara,Prakasha,Gowda, D. Channe
, p. 1332 - 1341 (2009)
Low-cost zinc is employed as a catalyst along with triethylsilane (TES) in a simple, straightforward, chemoselective reduction of various aldimines and ketimines to the corresponding secondary amines at room temperature and pressure.
Molybdenum nitrosyl complexes and their application in catalytic imine hydrogenation reactions
Dybov, Alexander,Blacque, Olivier,Berke, Heinz
, p. 652 - 659 (2011)
The reaction between [Mo(CO)4(NO)(ClAlCl3)] and the sterically hindered diphosphanes (P∩P) 1,3-bis(diisopropylphosphanyl)propane (dippp, a), 1,2-bis(diisopropylphosphanyl)ethane (dippe, b), 1,1′-bis(diisopropylphosphanyl)ferrocene (d
Cooperative catalysis of molybdenum with organocatalysts for distribution of products between amines and imines
Wu, Di,Bu, Qingqing,Guo, Cheng,Dai, Bin,Liu, Ning
, (2021/02/02)
Multi-amino groups and nitrogen donors compound was discovered as an organocatalyst for N-alkylation of alcohols with amines in the presence of Mo(CO)6. The Mo(CO)6/organocatalyst binary system has shown to be a highly active catalyst for the N-alkylation reaction between alcohols and amines with excellent tolerance of variable starting materials bearing different functional groups. Of particular note, this method possessing a superiority selectivity in the synthesis of N-alkylated amines or imines, which can be controlled by the reaction temperature. The cooperative catalysis mechanism in combination of Mo(CO)6 with organocatalyst was elucidated by control experiments.
New benzamide derivatives and their nicotinamide/cinnamamide analogs as cholinesterase inhibitors
Bilginer, Sinan,Koca, Mehmet
, (2021/06/30)
In this study, a total of 18 new benzamide/ nicotinamide/ cinnamamide derivative compounds were designed and synthesized for the first time (except B1 and B5) by conventional and microwave irradiation methods. The chemical structures of the synthesized co
Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
Kathuria, Lakshay,Samuelson, Ashoka G.
supporting information, (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.
Diethylsilane as a Powerful Reagent in Au Nanoparticle-Catalyzed Reductive Transformations
Louka, Anastasia,Kidonakis, Marios,Saridakis, Iakovos,Zantioti-Chatzouda, Elisavet-Maria,Stratakis, Manolis
, p. 3508 - 3514 (2020/06/02)
Diethylsilane (Et2SiH2), a simple and readily available dihydrosilane, that exhibits superior reactivity, as compared to monohydrosilanes, in a series of reductive transformations catalyzed by recyclable and reusable Au nanoparticles (1 mol-%) supported on TiO2. It reduces aldehydes or ketones almost instantaneously at ambient conditions. It can be used in a one pot rapid reductive amination procedure, in which premixing of aldehyde and amine is required prior to the addition of the reducing agent and the catalyst, even in a protic solvent. An unprecedented method for the synthesis of N-arylisoindolines is also shown in the reductive amination between o-phthalaldehyde and anilines. In this transformation, it is proposed that the intermediate N,2-diphenylisoindolin-1-imines are reduced stepwise to the isoindolines. Finally, Et2SiH2 readily reduces amides into amines in excellent yields and shorter reaction times relative to previously known analogous nano Au(0)-catalyzed protocols.
Catalyst- And solvent-free efficient access to: N -alkylated amines via reductive amination using HBpin
Bauri, Somnath,Pandey, Vipin K.,Rit, Arnab
, p. 3853 - 3857 (2020/07/27)
A sustainable approach which works under catalyst- and solvent-free conditions for the synthesis of structurally diverse secondary amines has been uncovered. This one-pot protocol works efficiently at room temperature and is compatible with a wide range of sterically and electronically diverse aldehydes and primary amines. Notably, this simple process offers scalability, excellent functional group tolerance, chemoselectivity, and is also effective at the synthesis of biologically relevant molecules. This journal is
Catalyst-Free and Solvent-Free Facile Hydroboration of Imines
Pandey, Vipin K.,Donthireddy, Siva Nagendra Reddy,Rit, Arnab
supporting information, p. 3255 - 3258 (2019/09/17)
A facile process for the catalyst-free and solvent-free hydroboration of aromatic as well as heteroaromatic imines is reported. This atom-economic methodology is scalable, compatible with sterically and electronically diverse imines, displaying excellent tolerance towards various functional groups, and works efficiently at ambient temperature in most of the cases, affording secondary amines in good to excellent yield after hydrolysis.
Visible-Light Photocatalytic Synthesis of Amines from Imines via Transfer Hydrogenation Using Quantum Dots as Catalysts
Xi, Zi-Wei,Yang, Lei,Wang, Dan-Yan,Pu, Chao-Dan,Shen, Yong-Miao,Wu, Chuan-De,Peng, Xiao-Gang
, p. 11886 - 11895 (2018/09/25)
CdSe/CdS core/shell quantum dots (QDs) can be used as stable and highly active photoredox catalysts for efficient transfer hydrogenation of imines to amines with thiophenol as a hydrogen atom donor. This reaction proceeds via a proton-coupled electron transfer (PCET) from the QDs conduction band to the protonated imine followed by hydrogen atom transfer from the thiophenol to the α-aminoalkyl radical. This precious metal free transformation is easy to scale up and can be carried out by a one-pot protocol directly from aldehyde, amine, and thiophenol. Additional advantageous features of this protocol include a wide substrate scope, high yield of the amine products, extremely low catalyst loading (0.001 mol %), high turnover number (105), and the mild reaction conditions of using visible light or sun light at room temperature in neutral media.
Well-Defined Amidate-Functionalized N-Heterocyclic Carbene -Supported Rare-Earth Metal Complexes as Catalysts for Efficient Hydroboration of Unactivated Imines and Nitriles
Huang, Zeming,Wang, Shaowu,Zhu, Xiancui,Yuan, Qingbing,Wei, Yun,Zhou, Shuangliu,Mu, Xiaolong
, p. 15069 - 15078 (2018/12/14)
Four amidate-functionalized N-heterocyclic carbene (NHC) rare-earth metal amido complexes [(κ2-N,O-κ1-L)2REN(SiMe3)2] (L = 1-(C6H5CONCH2CH2)-3-(CH3)3C6H2(N(CH)2NC)) [RE = Er (1), Y (2), Dy (3), Gd (4)] were synthesized by one-pot reactions of 2 equiv of (1-(C6H5CONHCH2CH2)-3-(CH3)3C6H2-(N(CH)2NCH))Br (H2LBr) with 5 equiv of KN(SiMe3)3 followed by treatment with 1 equiv of RECl3 in tetrahydrofuran at -40 °C. These complexes were fully characterized, and their catalytic activities toward hydroboration of unactivated imines and nitriles were investigated, and it was found that these complexes displayed excellent activities as well as remarkable functional group compatibility for imine and nitrile substrates such as halo-, alkyl-, hydroxyl-, N,N-dimethylamino-, and nitro- substituents. Among those, the chemoselectivity for this reaction among the common unsaturated functional groups was achieved in the order CO CN > C=N > CO2Et > CC in the current catalytic system, which may facilitate their further application in synthetic chemistry.
