1738-99-4Relevant academic research and scientific papers
An improved protocol for the selective hydroaminomethylation of arylethylenes
Routaboul, Lucie,Buch, Cathleen,Klein, Holger,Jackstell, Ralf,Beller, Matthias
, p. 7401 - 7405 (2005)
The hydroaminomethylation of arylethylenes with anilines proceeds under mild conditions in the presence of [Rh(cod)2BF4] and dppf as catalyst system to give the corresponding branched amphetamine derivatives in good selectivity and y
A Sustainable Palladium-Intercalated Montmorillonite Clay Catalytic System for Imine Hydrogenation under Mild Conditions
Gupta, Unnati,Krishnapriya,Sharma, Rakesh K
, p. 540 - 548 (2021)
A series of palladium nanoparticles (Pd NPs) intercalated montmorillonite clay catalysts is reported for hydrogenation of 3-diphenyl prop-2-en-1-imine under mild reaction conditions. Pd/clay catalyst was prepared by a simple wet-impregnation method, and t
Reaction of (1-azabuta-1,3-diene)tricarbonyliron(0) complexes with sodium borohydride under microwave conditions
Akisanya, Joseph,Danks, Timothy N.,Garman, Russell N.
, p. 240 - 243 (2000)
Reaction of (1-azabuta-1,3-diene)tricarbonyliron(0) complexes with sodium borohydride under microwave irradiation leads to formation of saturated secondary amines. When sodium borodeuteride is used for the reaction the products are 1,2,3-trideutero second
Ureate Titanium Catalysts for Hydroaminoalkylation: Using Ligand Design to Increase Reactivity and Utility
Man?en, Manfred,Deng, Danfeng,Zheng, Cameron H. M.,Dipucchio, Rebecca C.,Chen, Dafa,Schafer, Laurel L.
, p. 4550 - 4560 (2021/05/04)
Hydroaminoalkylation describes the atom-economical catalytic synthesis of amines by forming new Csp3-Csp3 bonds using readily available amine and alkene feedstocks. Herein, we describe an earth-abundant and cost-efficient titanium catalyst generated in si
Direct, Catalytic α-Alkylation of N-Heterocycles by Hydroaminoalkylation: Substrate Effects for Regiodivergent Product Formation
Daneshmand, Pargol,Dipucchio, Rebecca C.,Ezhova, Maria B.,Lenzen, Karst E.,Schafer, Laurel L.
supporting information, p. 11243 - 11250 (2021/08/03)
Saturated N-heterocycles are prevalent in pharmaceutical and agrochemical industries, yet remain challenging to catalytically alkylate. Most strategies for C-H activation of these challenging substrates use protected amines or high loadings of precious me
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.
Heterogeneous Ru/TiO2for hydroaminomethylation of olefins: multicomponent synthesis of amines
An, Jinghua,Gao, Zhuyan,Wang, Yehong,Zhang, Zhixin,Zhang, Jian,Li, Lu,Tang, Bo,Wang, Feng
supporting information, p. 2722 - 2728 (2021/04/21)
Synthesizing aminesviathe hydroaminomethylation (HAM) reaction of olefins, a multicomponent reaction, has been regarded as one of the most attractive methods compared with the traditional methods considering the atom economy and environmental friendliness. However, the use of homogeneous catalysts, complex ligands containing diphosphine or nitrogen, and base or acid additives has severely hampered the utilization of these methods. Herein, an efficient heterogeneous Ru/TiO2-catalyzed HAM reaction of olefins is developed without any additives. Various amines, including secondary and tertiary amines, can be successfully obtained from olefins including aromatic and aliphatic olefins. Systematic studies demonstrate the lower electron density of Ruδ+and the higher number of acid sites of Ru/TiO2, leading to the high HAM reaction activity of olefins. Most importantly, nitrobenzene derivatives can also be transformed to the corresponding products over Ru/TiO2in excellent yields.
A highly efficient Co-based catalyst fabricated by coordination-assisted impregnation strategy towards tandem catalytic functionalization of nitroarenes with various alcohols
Li, Guangming,Li, Jingfang,Li, Weizuo,Li, Xuewei,Li, Zhibin,Mao, Guijie,She, Wei,Wang, Jing
, p. 462 - 474 (2021/11/11)
A well-defined hexamethylenetetramine (abbreviated as HMTA) based two-dimensional (2D) MOFs metalloligand (termed Zn-HMTA), with free uncoordinated tertiary amine groups, has been synthesized via solution diffusion method for the first time. The crystal structure of 2D Zn-HMTA metalloligand was determined by the single crystal X-ray diffraction (SCXRD). The SCXRD and X-ray photoelectron spectroscopy (XPS) analyses have revealed that the 2D Zn-HMTA metalloligand is rich in- free tertiary amine groups, which are of strong coordination ability to transition metal ions (e.g. Ni2+, Co2+, Zn2+, Cu2+). As a result, a 2D bimetallic Co@Zn-HMTA MOFs was synthesized via coordination-assisted impregnation (CAI) strategy attributed to the unique feature of strong coordinated ability of free tertiary amine groups. Furthermore, a series of self-supported Co-ZnO-CN nanocatalysts were afforded upon the as-synthesized Co@Zn-HMTA MOFs served as a self-sacrificial template for pyrolysis at different temperatures. The optimized catalyst (termed as Co-ZnO@CN-CAI) demonstrated the excellent catalytic performance for hydrogenation-alkylation tandem reaction in comparison with the classic ZnO@CN composite (derived from Zn-HMTA MOFs) supported metallic Co catalyst (Co-ZnO@CN-IWI) prepared by incipient wetness impregnation method. Moreover, the kinetic study was also performed to confirm that the alkylation is the rate-determining step in the hydrogenation-alkylation tandem reaction. The origin of enhanced catalytic performance of Co-ZnO@CN-CAI and the role of Co@Zn-HMTA MOFs precursor have been explored by way of various characterizations, e.g. HADDF-STEM-EDS, SEM-EDS, 13C MAS NMR, XRD, Raman and XPS, etc. It is anticipated that the prepared low-cost and easily prepared 2D Zn-HMTA metalloligand will become a general template for synthesis of highly self-supported catalysts with coordination-assisted impregnation strategy (CAI) for various catalytic reactions.
PH-Mediated Selective Synthesis of N-Allylic Alkylation or N-Alkylation Amines with Allylic Alcohols via an Iridium Catalyst in Water
Luo, Nianhua,Zhong, Yuhong,Shui, Hongling,Luo, Renshi
supporting information, p. 15509 - 15521 (2021/11/01)
Amination of allylic alcohols is an effective approach in the facile synthesis of N-allylic alkylation or N-alkylation amines. Recently, a series of catalysts were devised to push forward this transformation. However, current synthetic methods are typical
Chemoselective heterogeneous iridium catalyzed hydrogenation of cinnamalaniline
Savela, Risto,Shcherban, Nataliya D.,Melander, Marko M.,Bezverkhyy, Igor,Simakova, Irina L.,L?ngvik, Otto,Kholkina, Ekaterina,Schindler, Tamara,Krauβ, Annabelle,Honkala, Karoliina,Murzin, Dmitry Yu.,Leino, Reko
, p. 1481 - 1496 (2021/03/14)
Selective hydrogenation of unsaturated imines over heterogeneous catalysts is an ecologically feasible and effective way to produce commercially valuable saturated imines and unsaturated amines under mild conditions, avoiding the utilization of toxic halides. The liquid-phase hydrogenation of a model imine, cinnamalaniline, over Ir, Ru, Pd and Au catalysts was studied in polar protic (methanol, 2-propanol), polar aprotic (methyltert-butyl ether) and non-polar aprotic (toluene) solvents at 40-80 °C under atmospheric hydrogen pressure. Different metal oxides (Al2O3, ZrO2, SiO2) and carbon composites based on carbon nitrides synthesized by pyrolysis of ethylenediamine or melamine modified by KOH, HNO3, NH4Cl or TEOS (including template KIT-6), porous carbon (samples prepared by pyrolysis of sucrose, including template KIT-6) and mesoporous carbon Sibunit were applied to study the effect of the support. Among the tested metals, iridium exhibited the most promising catalytic performance in terms of hydrogenation activity and chemoselectivity towards unsaturated amine. The use of Ir on carbon nitrides (C3N4-NH4Cl, CxNy-KIT-6) and amphoteric metal oxides (ZrO2, Al2O3) in nonpolar aprotic toluene solvent provided the best selectivity towards unsaturated amine by minimizing oligomerization. Computational studies indicate that the selective hydrogenation of the CN group on Ir results from a favorable cinnamalaniline adsorption geometry at high surface coverage. Comparable heterogeneously catalyzed highly chemoselective hydrogenation of unsaturated imine into unsaturated amine under atmospheric hydrogen pressure and low temperatures has not been reported previously.
