5689-74-7Relevant academic research and scientific papers
Hydroalkylation of Styrenes with Benzylamines by Potassium Hydride
Chiba, Shunsuke,Pang, Jia Hao,Takita, Ryo,Wang, Bin,Watanabe, Kohei
, (2021/09/25)
A method for the synthesis of 1,3-diarylpropylamines through hydroalkylation of styrenes with benzylamines by potassium hydride has been developed. The protocol is initiated by solvothermal treatment of benzylamines with KH at 100 °C to generate deprotonated anionic species, which undergo selective C-alkylation with arylalkenes at 0 °C to ambient temperature to afford 1,3-diarylpropylamines as the major product.
Direct azidation of allylic/benzylic alcohols and ethers followed by the click reaction: One-pot synthesis of 1,2,3-triazoles and 1,2,3-triazole moiety embedded macrocycles
Naveen,Babu, Srinivasarao Arulananda,Aslam, Nayyar Ahmad,Sandhu, Akshey,Singh, Dharmendra Kumar,Rana, Ameet
, p. 7026 - 7045 (2015/08/24)
Investigations on the one-pot direct azidation of allylic/benzylic alcohols or their methyl ethers followed by the click reaction are reported. Two methods involving sequential reactions were developed for synthesizing substituted 1,2,3-triazoles starting from allylic/benzylic alcohols. The first method involves magnetically separable nano Fe3O4-catalyzed direct azidation of various allylic/benzylic alcohols with TMSN3 as the first step followed by the Cu-catalyzed click reaction of azides with alkynes as the second step. The second method involves Cu(OTf)2-catalyzed direct azidation of allylic/benzylic alcohols and their methyl ethers with TMSN3 as the first step followed by the click reaction of azides with alkynes as the second step. In this method, Cu(OTf)2 served as a single catalyst for both the azidation of alcohol and click reaction steps. Utility of this protocol has been revealed by synthesizing new classes of polyether systems and macrocyles embedded with the 1,2,3-triazole and 1,3-diyne units.
Magnetically separable nano Fe3O4 catalyzed direct azidation of allylic and benzylic alcohols followed by copper-catalyzed click reaction
Aslam, Nayyar Ahmad,Babu, Srinivasarao Arulanda,Singh, Dharmendra Kumar,Rana, Ameet
supporting information, p. 2201 - 2207 (2014/11/08)
A competent one-pot method comprising magnetically separable nano Fe 3O4 catalyzed direct azidation of allylic and benzylic alcohols followed by the copper-catalyzed click reaction of the corresponding azides with alkynes is reported. This method gave a direct access to several 1,2,3-triazoles starting from various allylic and benzylic alcohols via their respective azides. Georg Thieme Verlag Stuttgart New York.
Primary amines by transfer hydrogenative reductive amination of ketones by using cyclometalated IrIII catalysts
Talwar, Dinesh,Salguero, Noemi Poyatos,Robertson, Craig M.,Xiao, Jianliang
supporting information, p. 245 - 252 (2014/01/17)
Cyclometalated iridium complexes are found to be versatile catalysts for the direct reductive amination (DRA) of carbonyls to give primary amines under transfer-hydrogenation conditions with ammonium formate as both the nitrogen and hydrogen source. These complexes are easy to synthesise and their ligands can be easily tuned. The activity and chemoselectivity of the catalyst towards primary amines is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Both aromatic and aliphatic primary amines were obtained in high yields. Moreover, a first example of homogeneously catalysed transfer-hydrogenative DRA has been realised for β-keto ethers, leading to the corresponding β-amino ethers. In addition, non-natural α-amino acids could also be obtained in excellent yields with this method. Reduce the work! A broad range of ketones have been successfully aminated to afford primary amines under transfer-hydrogenation conditions by using ammonium formate as the amine source and 0.1 mol % of a cyclometalated IrIII catalyst (see scheme). Copyright
CATALYST COMPOUNDS
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Paragraph 00163; 00170, (2013/11/05)
The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.
Asymmetric synthesis of chiral primary amines by transfer hydrogenation of N -(tert -Butanesulfinyl)ketimines
Guijarro, David,Pablo, Oscar,Yus, Miguel
supporting information; experimental part, p. 5265 - 5270 (2010/10/21)
(Figure presented) The diastereoselective reduction of (R)-N-(tert- butanesulfinyl)ketimines by a ruthenium-catalyzed asymmetric transfer hydrogenation process in isopropyl alcohol, followed by desulfinylation of the nitrogen atom, is an excellent method to prepare highly enantiomerically enriched α-branched primary amines (up to >99% ee) in short reaction times (1-4 h). (1S,2R)-1-Amino-2-indanol has been shown to be a very efficient ligand to perform this transformation. Ketimines bearing either an aryl or a heteroaryl group and an alkyl group as substituents of the iminic carbon atom are very good substrates for this process. The reduction of a dialkyl ketimine could also be achieved, affording the expected amine with moderate optical purity (69% ee). Some amines which are precursors of very interesting biologically and pharmacologically active compounds have been prepared in excellent yields and enantiomeric excesses.
Base-catalyzed anti-Markovnikov hydroamination of vinylarenes - Scope, limitations and computational studies
Horrillo-Martinez, Patricia,Hultzsch, Kai C.,Gil, Adria,Branchadell, Vicenc
, p. 3311 - 3325 (2008/02/10)
The hydroamination of vinylarenes with primary and secondary amines was studied with catalytic amounts as low as 2 mol-% of LiN(SiMe3) 2/TMEDA. Reactions proceeded readily at 120°C in the absence of solvent to give selective anti-Markovnikov addition. Slow addition was observed at 25°C with either electron-deficient p-chlorostyrene or secondary cyclic amines such as pyrrolidine, piperidine, or morpholine. Primary amines were prone to a second hydroamination reaction to form tertiary amine byproducts. The selectivity for the mono(hydroamination) products could be improved with a two-fold excess of the amine. KN(SiMe3)2 showed higher catalytic activity but lower selectivity in comparison to that of LiN(SiMe 3)2, resulting in undesired C-H-activation by-products. The mechanism of the lithium-catalyzed hydroamination and the influence of TMEDA was studied with density functional theory. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Redox-photosensitized aminations of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia
Yasuda, Masahide,Kojima, Ryuji,Tsutsui, Hiroshi,Utsunomiya, Daigo,Ishii, Kazuaki,Jinnouchi, Koutaro,Shiragami, Tsutomu
, p. 7618 - 7624 (2007/10/03)
1,2,4-Triphenylbenzene and 2,2′-methylenedioxy-1,1′ -binaphthalene successfully photosensitized the aminations of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia and primary amines in the presence of m- or p-dicyanobenzene, which gave the 4-amino-1,2-benzocycloalkenes, 3-amino-1-arylpropanes, and 7-amino-5-(p-cyanophenyl)bicyclo[2.2.1]hept-2-ene, respectively. A key pathway for the photosensitized amination is the hole transfer from the cation radicals of the sensitizers that were generated by photoinduced electron transfer to the electron acceptors to the substrates. Therefore, it was found that the relationships in oxidation potentials between the sensitizers and the substrates and the positive charge distribution of the cation radicals of the substrates were important factors for the efficient amination.
Process for producing optically active 3,3,3-Trifluoro-2-Hydroxy-2-Methylpropionic acid, and salt thereof
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, (2008/06/13)
There are disclosed are a diastereomer salt of formula (1): a process for producing the same, a process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid of formula (2′): a novel optically active amine compound of formula (4): a novel optically active amine compound of formula (8): an imine compound of formula (7) or (11):
Polymer bound iminodicarbonate: A new ammonia equivalent for solid-phase synthesis of primary amines
Subramanyam
, p. 6537 - 6540 (2007/10/03)
A polymer bound iminodicarbonate has been designed and its use in solid-phase synthesis of primary amines is reported. (C) Elsevier Science Ltd.
