15258-43-2Relevant articles and documents
Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment
Deng, Danfeng,Hu, Bowen,Zhang, Ziyu,Mo, Shengkai,Yang, Min,Chen, Dafa
, p. 2218 - 2226 (2019/05/21)
Six Cp?Ir complexes containing NN-bitentate chelate ligands [Cp?IrCl(C5H4CH2C5H3OH)][Cl] (1), [Cp?IrCl(C5H4CH2C5H3O)] (2), [Cp?IrCl(C5H4C5H3OH)] [Cl] (3), [Cp?IrCl(C5H4CH2C5H4)][Cl] (4), [Cp?IrCl(CH3OC5H3CH2C5H3OCH3)][Cl] (5), and [Cp?IrCl(CH3OC5H3CH2C5H3OH)][Cl] (6) were synthesized and characterized. Complex 1 could be transformed to 2 when reacted with NaOtBu or NEt3 via -OH deprotonation. These six complexes were tested as catalysts for mono-N-alkylation of amines with trialkyl amines, and complex 1 exhibited highest activity. The coupling reactions proceed under air condition, with 1 mol % catalyst loading without extra base in methanol at 120 °C and can be further accelerated by adding NR3·HCl.
Cobalt-Catalyzed Reductive Alkylation of Amines with Carboxylic Acids
Emayavaramban, Balakumar,Chakraborty, Priyanka,Sundararaju, Basker
, p. 3089 - 3093 (2018/12/11)
Direct reductive alkylation of amines with carboxylic acid is carried out by using an inexpensive, air-stable cobalt/triphos catalytic system with molecular hydrogen as the reductant. This efficient synthetic method proceeds through reduction and condensation, followed by reduction of the in situ-generated imine into the amine in a green catalytic process.
Hydrogenation and: N-Alkylation of anilines and imines via transfer hydrogenation with homogeneous nickel compounds
Benitez-Medina, G. Eliad,García, Juventino J.
supporting information, p. 17579 - 17587 (2019/12/23)
The nickel-catalyzed N-Alkylation of a variety of arylamines via transfer hydrogenation in the absence of pressurized hydrogen and basic or acidic additives was achieved in a tandem reaction. This process was further extended to the CN bond reduction and N-Alkylation of a variety of imines with ethanol, the latter acting as a hydrogen and acetaldehyde source, which allowed for the reduction and subsequent condensation to yield the corresponding N-Alkylated products.
Tailored Cobalt-Catalysts for Reductive Alkylation of Anilines with Carboxylic Acids under Mild Conditions
Liu, Weiping,Sahoo, Basudev,Spannenberg, Anke,Junge, Kathrin,Beller, Matthias
supporting information, p. 11673 - 11677 (2018/09/10)
The first cobalt-catalyzed hydrogenative N-methylation and alkylation of amines with readily available carboxylic acid feedstocks as alkylating agents and H2 as ideal reductant is described. Combination of tailor-made triphos ligands with cobalt(II) tetrafluoroborate significantly improved the efficiency, thus promoting the reaction under milder conditions. This novel protocol allows for a broad substrate scope with good functional group tolerance, even in the presence of reducible alkenes, esters, and amides.
An Efficient Metal-Free Method for the Denitrosation of Aryl N-Nitrosamines at Room Temperature
Chaudhary, Priyanka,Korde, Rishi,Gupta, Surabhi,Sureshbabu, Popuri,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
supporting information, p. 556 - 561 (2017/11/13)
A simple and practical method for the denitrosation of aryl N-nitrosamines to secondary amines is reported under metal-free conditions using iodine and triethylsilane. Several reduction-susceptible functional groups such as alkene, alkyne, nitrile, nitro, aldehyde, ketone and ester were found to be very stable during the denitrosation, which is remarkable. Broad substrate scope, room temperature reactions and excellent yields are the additional features of the current methodology. (Figure presented.).
Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines
Cabrero-Antonino, Jose R.,Alberico, Elisabetta,Junge, Kathrin,Junge, Henrik,Beller, Matthias
, p. 3432 - 3442 (2016/05/19)
A broad range of secondary and tertiary amides has been hydrogenated to the corresponding amines under mild conditions using an in situ catalyst generated by combining [Ru(acac)3], 1,1,1-tris(diphenylphosphinomethyl)ethane (Triphos) and Yb(OTf)3. The presence of the metal triflate allows to mitigate reaction conditions compared to previous reports thus improving yields and selectivities in the desired amines. The excellent isolated yields of two scale-up experiments corroborate the feasibility of the reaction protocol. Control experiments indicate that, after the initial reduction of the amide carbonyl group, the reaction proceeds through the reductive amination of the alcohol with the amine arising from collapse of the intermediate hemiaminal.
Thiol activated prodrugs of sulfur dioxide (SO2) as MRSA inhibitors
Pardeshi, Kundansingh A.,Malwal, Satish R.,Banerjee, Ankita,Lahiri, Surobhi,Rangarajan, Radha,Chakrapani, Harinath
, p. 2694 - 2697 (2015/06/08)
Drug resistant infections are becoming common worldwide and new strategies for drug development are necessary. Here, we report the synthesis and evaluation of 2,4-dinitrophenylsulfonamides, which are donors of sulfur dioxide (SO2), a reactive sulfur species, as methicillin-resistant Staphylococcus aureus (MRSA) inhibitors. N-(3-Methoxyphenyl)-2,4-dinitro-N-(prop-2-yn-1-yl)benzenesulfonamide (5e) was found to have excellent in vitro MRSA inhibitory potency. This compound is cell permeable and treatment of MRSA cells with 5e depleted intracellular thiols and enhanced oxidative species both results consistent with a mechanism involving thiol activation to produce SO2.
Nickel-catalyzed amination of Aryl chlorides with ammonia or ammonium salts
Green, Rebecca A.,Hartwig, John F.
supporting information, p. 3768 - 3772 (2015/03/18)
The nickel-catalyzed amination of aryl chlorides to form primary arylamines occurs with ammonia or ammonium sulfate and a well-defined single-component nickel(0) precatalyst containing a Josiphos ligand and an η2-bound benzonitrile ligand. This system also catalyzes the coupling of aryl chlorides with gaseous amines in the form of their hydrochloride salts. Simple alternative: The title reaction, which results in primary arylamines, is catalyzed by well-defined single-component nickel(0) precatalysts containing a Josiphos ligand and an η2-bound benzonitrile ligand. This system also catalyzes the coupling of aryl chlorides with gaseous amines in the form of their hydrochloride salts.
Palladium-Catalyzed Amination of N-Free 2-Chloro-7-azaindole
Plas, Aurélie,Martin, Camille,Joubert, Nicolas,Viaud-Massuard, Marie-Claude
supporting information, p. 4710 - 4713 (2015/10/12)
A simple and efficient procedure for the Pd-catalyzed amination of N-free 2-chloro-7-azaindole is described, using either primary or secondary amines. An optimized combination of Brettphos, a Brettphos precatalyst, and LiHMDS in THF led us to a novel methodology, applied to various functionalized amines to study the scope of the reaction. This is the first report of cross-coupling amination on N-free 2-chloro-7-azaindole.
Palladium-catalyzed amination of aryl chlorides and bromides with ammonium salts
Green, Rebecca A.,Hartwig, John F.
supporting information, p. 4388 - 4391 (2015/01/08)
We report the palladium-catalyzed coupling of aryl halides with ammonia and gaseous amines as their ammonium salts. The coupling of aryl chlorides and ortho-substituted aryl bromides with ammonium sulfate forms anilines with higher selectivity for the primary arylamine over the diarylamine than couplings with ammonia in dioxane. The resting state for the reactions of aryl chlorides is different from the resting state for the reactions of aryl bromides, and this change in resting states is proposed to account for a difference in selectivities for reactions of the two haloarenes.
