15286-54-1Relevant academic research and scientific papers
Vanadium-and chromium-catalyzed dehydrogenative synthesis of imines from alcohols and amines
Madsen, Robert,Miao, Yulong,Samuelsen, Simone V.
supporting information, p. 1328 - 1335 (2021/05/29)
Vanadium(IV) tetraphenylporphyrin dichloride and chromium(III) tetraphenylporphyrin chloride have been developed as catalysts for the acceptorless dehydrogenation of alcohols. The catalysts have been applied to the direct synthesis of imines in overall good yields from a variety of alcohols and amines. The transformations are proposed to proceed by metal?ligand bifunctional pathways with an outer-sphere transfer of two hydrogen atoms from the alcohol to the metal porphyrin complexes. The results show that vanadium and chromium catalysts can also be employed for the dehydrogenation of alcohols with the release of hydrogen gas, and they may represent valuable alternatives to other catalysts based on Earth-abundant metals.
Aerobic oxidative coupling of alcohols and amines towards imine formation by a dicopper(I,I) catalyst
Dutta, Indranil,De, Subhabrata,Yadav, Sudhir,Mondol, Ranajit,Bera, Jitendra K.
, p. 117 - 124 (2017/09/30)
A dicopper(I,I) complex [Cu2(L1) (Cl)2] (1), bearing a Cu2Cl2 core spanned by a naphthyridine–diimine ligand is synthesized by the treatment of CuCl with 2,7–bis(N–mesitylmethylimino)–1,8–naphthyridine (L1). The catalytic efficacy of 1 is assessed for aerobic oxidative synthesis of imines from alcohols and amines. The title complex is found to be an excellent catalyst for a wide variety of alcohols and amines. Kinetic experiments revealed the involvement of both copper ions in the aerobic oxidation process. The general utility of naphthyridine based ligands to favour a possible bimetallic pathway for a catalytic reaction is demonstrated here.
General, green, and scalable synthesis of imines from alcohols and amines by a mild and efficient copper-catalyzed aerobic oxidative reaction in open air at room temperature
Tian, Haiwen,Yu, Xiaochun,Li, Qiang,Wang, Jianxin,Xu, Qing
supporting information, p. 2671 - 2677,7 (2012/12/12)
A general, green, and scalable synthesis of the useful imines and a,b-unsaturated imines is successfully achieved by a low-loading and powerful, mild and efficient copper-catalyzed aerobic oxidative reaction of alcohols and amines in the open air at room temperature under base- and dehydrating reagent-free conditions. This practical reaction can use air as the economic and green oxidant, tolerates a wide range of substrates, can afford high yields of the target imines on a large scale, and produces water as the only by-product, and thus being the best imination method as yet using alcohols and amines directly.
Highly regioselective control of 1,2-addition of organolithiums to α,β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran: A facile and eco-friendly access to allylic alcohols and amines
Pace, Vittorio,Castoldi, Laura,Hoyos, Pilar,Sinisterra, José Vicente,Pregnolato, Massimo,Sánchez-Montero, Ma. José
supporting information; experimental part, p. 2670 - 2675 (2011/04/23)
Very high regioselective 1,2-addition of organolithiums to α,α-unsaturated carbonyl-like compounds (ketones, aldehydes, and imines) in the presence of LiBr was achieved by carrying out reactions in the sustainable solvent 2-methyltetrahydrofuran. Excellent yields (in isolated product) of allylic alcohols and allylic amines were recovered under a simple experimental procedure at 0 °C.
Enantioselective rhodium-catalyzed [4 + 2] cycloaddition of α,β-unsaturated imines and isocyanates
Oberg, Kevin M.,Rovis, Tomislav
supporting information; experimental part, p. 4785 - 4787 (2011/05/16)
A [4 + 2] cycloaddition of α,β-unsaturated imines and isocyanates catalyzed by a phosphoramidite-rhodium complex provides pyrimidinones in good yields and high enantioselectivities.
Oxidation of aliphatic α,β-unsaturated aldimines to amides specifically by oxone with AlCl3
Lu, Zhou,Peng, Lijun,Wu, Wentao,Wu, Longmin
, p. 2357 - 2366 (2008/09/21)
α,β-Unsaturated aldimines were specifically oxidized to amides with Oxone in the presence of AlCl3 as a Lewis acid in CH2Cl2. No migration of aryl group occurred in the rearrangement reaction. Copyright Taylor & Francis Group, LLC.
Eco-friendly synthesis of imines by ultrasound irradiation
Guzen, Karla P.,Guarezemini, Alexandre S.,órf?o, Aline T.G.,Cella, Rodrigo,Pereira, Claudio M.P.,Stefani, Hélio A.
, p. 1845 - 1848 (2008/02/05)
A series of imines was synthesized by an ultrasound-assisted reaction of aldehydes and primary amines using silica as the promoter. Products were obtained in high yields even in large scale synthesis.
A simple protocol for direct reductive amination of aldehydes and ketones using potassium formate and catalytic palladium acetate
Basu, Basudeb,Jha, Satadru,Bhuiyan, Md. Mosharef H.,Das, Pralay
, p. 555 - 557 (2007/10/03)
A method for direct reductive amination of aldehydes and ketones, including α,β-unsaturated carbonyl compounds, has been developed, which requires potassium formate as reductant and palladium acetate as catalyst. Suitable amines include both primary and secondary aliphatic and aromatic amines.
Electronic and steric control in regioselective addition reactions of organolithium reagents with enaldimines
Tomioka,Shioya,Nagaoka,Yamada
, p. 7051 - 7054 (2007/10/03)
A reaction mode of imines derived from naphthalene-1-carbaldehyde and acyclic α,β-unsaturated aldehydes with organolitium reagents was dependent on the characteristic nature of a substituent on the imine nitrogen atom. An imine having an electron-withdrawing aryl group on the nirtogen atom behaves as a 1,2-directing imine toward organolithium reagents. In contrast, an imine bearing an alkyl or a bulky aryl group favors 1,4-addition of organolithium reagents. Electronic and steric tuning of a substituent on the imine nitrogen atom for a reaction mode was rationalized on the basis of molecular orbital calculations.
The first example of asymmetric induction in an anionic amino-Cope rearrangement
Allin, Steven M.,Button, Martin A. C.
, p. 3345 - 3348 (2007/10/03)
The anionic amino-Cope rearrangement of suitably functionalized acyclic 3-amino-1,5-diene substrates has been achieved and we report the first example of an asymmetric anionic amino-Cope rearrangement to yield an enantiomerically enriched product (75% e.e.). The absolute stereochemistry of the products has been verified and transition state models are proposed to rationalize the stereochemical outcome.
