Construction of α-alkylated amines by Iridium Complexes-Catalyzed One-Step Transfer Hydrogenation of C=C and C=N Bond

Hydrogenation of C=C bond and reductive amination is important transformation utilized in chemistry. An efficient and facile one-pot transfer hydrogenation of C=C bond and reductive amination of C=N bond of enones and amines was reported using the iridium complexes as catalysts and formic acid as hydrogen source in aqueous medium, which shows environmentally friendly. In this catalytic system, a wide range of α-alkylated amine compounds were obtained in excellent yields by one-pot transfer hydrogenation of C=C bond and reductive amination. The practical application of this protocol is characterized by gram-scale transformation.

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A Photo-Enzymatic Cascade to Transform Racemic Alcohols into Enantiomerically Pure Amines

Catalysts ◽

10.3390/catal9040305 ◽

2019 ◽

Vol 9 (4) ◽

pp. 305 ◽

Cited By ~ 7

Author(s):

Jenő Gacs ◽

Wuyuan Zhang ◽

Tanja Knaus ◽

Francesco G. Mutti ◽

Isabel W.C.E. Arends ◽

...

Keyword(s):

Aromatic Compounds ◽

Reductive Amination ◽

Aerobic Oxidation ◽

Secondary Alcohols ◽

One Pot ◽

Enantiomerically Pure ◽

Step Procedure ◽

Wide Range ◽

Aldehydes And Ketones ◽

One Step

The consecutive photooxidation and reductive amination of various alcohols in a cascade reaction were realized by the combination of a photocatalyst and several enzymes. Whereas the photocatalyst (sodium anthraquinone-2-sulfonate) mediated the light-driven, aerobic oxidation of primary and secondary alcohols, the enzymes (various ω-transaminases) catalyzed the enantio-specific reductive amination of the intermediate aldehydes and ketones. The system worked in a one-pot one-step fashion, whereas the productivity was significantly improved by switching to a one-pot two-step procedure. A wide range of aliphatic and aromatic compounds was transformed into the enantiomerically pure corresponding amines via the photo-enzymatic cascade.

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One-Pot Transfer Hydrogenation Reductive Amination of Aldehydes and Ketones by Iridium Complexes “on Water”

European Journal of Organic Chemistry ◽

10.1002/ejoc.202001097 ◽

2020 ◽

Author(s):

Lu Ouyang ◽

Yanping Xia ◽

Jianhua Liao ◽

Renshi Luo

Keyword(s):

Reductive Amination ◽

Transfer Hydrogenation ◽

Iridium Complexes ◽

One Pot ◽

Aldehydes And Ketones

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Chemoselective Transfer Hydrogenation of α,β-Unsaturated Ketones Catalyzed by Iridium Complexes

SynOpen ◽

10.1055/s-0040-1706022 ◽

2021 ◽

Vol 05 (01) ◽

pp. 36-42

Author(s):

Renshi Luo ◽

Yanping Xia ◽

Lu Ouyang ◽

Jianhua Liao ◽

Xiao Yang

Keyword(s):

Formic Acid ◽

Functional Groups ◽

Organic Solvents ◽

Mixed Solvents ◽

Transfer Hydrogenation ◽

Scale Transformation ◽

Iridium Complexes ◽

Practical Application ◽

Unsaturated Ketones ◽

Electron Withdrawing Substituents

AbstractEfficient chemoselective transfer hydrogenation of the C=C bond of α,β-unsaturated ketones has been developed, using the iridium complexes containing pyridine-imidazolidinyl ligands as catalysts and formic acid as a hydrogen source. In comparison with organic solvents or H2O as solvent, the mixed solvents of H2O and MeOH are critical for a high catalytic chemoselective transformation. This chemoselective transfer hydrogenation can be carried out in air, which is operationally simple, allowing a wide variety of α,β-unsaturated substrates with different functional groups (electron-donating and electron-withdrawing substituents) leading to chemoselective transfer hydrogenation in excellent yields. The practical application of this protocol is demonstrated by a gram-scale transformation.

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Direct reductive amination of aldehydes using lithium-arene(cat.) as reducing system. A simple one-pot procedure for the synthesis of secondary amines

Tetrahedron Letters ◽

10.1016/j.tetlet.2012.04.054 ◽

2012 ◽

Vol 53 (25) ◽

pp. 3156-3160 ◽

Cited By ~ 26

Author(s):

Fabiana Nador ◽

Yanina Moglie ◽

Andrés Ciolino ◽

Adriana Pierini ◽

Viviana Dorn ◽

...

Keyword(s):

Reductive Amination ◽

Secondary Amines ◽

One Pot ◽

System A

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One-Step Direct Amination of Nanodiamond Surface and Facile Separation by Viscosity Gradient Centrifugation

10.3762/bxiv.2019.127.v1 ◽

2019 ◽

Author(s):

Nianshun Yang ◽

Jean Felix Mukerabigwi ◽

Xueying Huang ◽

Yuyang Sun ◽

Juanxiao Cai ◽

...

Keyword(s):

Gradient Centrifugation ◽

Mechanochemical Reaction ◽

Distribution Analysis ◽

One Pot ◽

Direct Amination ◽

Wide Range ◽

One Step ◽

Ft Ir ◽

Synthesis Procedure ◽

Mechanochemical Reactions

Abstract: The introduction of terminal amine functional group on nanodiamond (ND) surface has been proposed as the key strategy to enable further synthesis of various ND derivatives for a wide range of application including sensors and biomedicine. Nevertheless, it is still challenging to develop a successful synthesis procedure to achieve monodispersed ND-NH2 mostly due to the undesirable high agglomeration effect of ND particles and complex synthetic steps which dramatically limit their practical use. In this work, we demonstrate a facile approach to obtain the direct amination of the ND surface, through a one pot mechanochemical reaction using ball milling in the presence of NH4Cl. To obtain monodispersed ND-NH2, a straightforward process by virtue of viscosity gradient centrifugation is adopted using aqueous polyvinylpyrrolidone (PVP) and glycerol. The results show a successful synthesis of ND-NH2 as evidenced by FT-IR and ζ–potential analysis. Moreover, the aminated ND particles morphology and size distribution analysis by TEM and DLS, respectively, show that using viscosity gradient built from aqueous PVP can achieve a better separation of NDs by size. Therefore, the findings suggested that the application of mechanochemical reactions and viscosity gradient centrifugation can be used to achieve homogeneous and monodispersed functionalized NDs for further specific technical applications.

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