A Photoredox-Catalyzed Four Component Reaction for the Atom-Efficient Synthesis of Complex Secondary Amines

2020 ◽  
Author(s):  
Lisa Marie Kammer ◽  
Matthias Krumb ◽  
Benjamin Spitzbarth ◽  
Benjamin Lipp ◽  
Jonas Kühlborn ◽  
...  
Keyword(s):  
Secondary Amines ◽  
Efficient Synthesis ◽  
One Pot ◽  
Simultaneous Formation ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Reaction Proceeds ◽  
Styrene Derivatives ◽  
The One ◽  
Single Bonds

The one-pot sulfonylation/aminoalkylation of styrene derivatives furnishing highly substituted gamma-sulfonylamines was accomplished through a photoredox-catalyzed four-component reaction. Apart from one molecule of water and the sodium counterion of the sulfinate, all atoms of the starting materials are transferred to the final product, rendering this process highly atom-efficient. The operationally simple protocol allows for the simultaneous formation of three new single bonds (C–S, C–N, and C–C) and therefore grants rapid access to structurally diverse products. The reaction proceeds under mild conditions in aqueous acetonitrile and shows a broad scope, including natural products and drug-like molecules.

A Photoredox-Catalyzed Four Component Reaction for the Atom-Efficient Synthesis of Complex Secondary Amines

2020 ◽  
Author(s):  
Lisa Marie Kammer ◽  
Matthias Krumb ◽  
Benjamin Spitzbarth ◽  
Benjamin Lipp ◽  
Jonas Kühlborn ◽  
...  
Keyword(s):  
Secondary Amines ◽  
Efficient Synthesis ◽  
One Pot ◽  
Simultaneous Formation ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Reaction Proceeds ◽  
Styrene Derivatives ◽  
The One ◽  
Single Bonds

The one-pot sulfonylation/aminoalkylation of styrene derivatives furnishing highly substituted gamma-sulfonylamines was accomplished through a photoredox-catalyzed four-component reaction. Apart from one molecule of water and the sodium counterion of the sulfinate, all atoms of the starting materials are transferred to the final product, rendering this process highly atom-efficient. The operationally simple protocol allows for the simultaneous formation of three new single bonds (C–S, C–N, and C–C) and therefore grants rapid access to structurally diverse products. The reaction proceeds under mild conditions in aqueous acetonitrile and shows a broad scope, including natural products and drug-like molecules.

scholarly journals Facile Synthesis of COF-Supported Reduced Pd-Based Catalyst for One-Pot Reductive Amination of Aldehydes

Catalysts ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 287
Author(s):  
Jianguo Liu ◽  
Mingyue Zhang ◽  
Longlong Ma
Keyword(s):  
Heterogeneous Catalysts ◽  
Reductive Amination ◽  
Secondary Amines ◽  
Metallic State ◽  
One Pot ◽  
Effective Synthesis ◽  
Pharmaceutical Industries ◽  
The One ◽  
Heterocyclic Aldehydes ◽  
Supported Pd

Dibenzylamine motifs are an important class of crucial organic compounds and are widely used in fine chemical and pharmaceutical industries. The development of the efficient, economical, and environmentally friendly synthesis of amines using transition metal-based heterogeneous catalysts remains both desirable and challenging. Herein, we prepared the covalent organic framework (COF)-supported heterogeneous reduced COF-supported Pd-based catalyst and used it for the one-pot reductive amination of aldehydes. There are both Pd metallic state and oxidated Pdσ+ in the catalysts. Furthermore, in the presence of the reduced COF-supported Pd-based catalyst, many aromatic, aliphatic, and heterocyclic aldehydes with various functional groups substituted were converted to their corresponding amines products in good to excellent selectivity (up to 91%) under mild reaction conditions (70 °C, 2 h, NH3, 20 bar H2). This work expands the covalent organic frameworks for the material family and its support catalyst, opening up new catalytic applications in the economical, practical, and effective synthesis of secondary amines.

scholarly journals Tandem four-component reaction for efficient synthesis of dihydrothiophene with substituted amino acid ethyl esters

RSC Advances ◽  
2018 ◽  
Vol 8 (40) ◽  
pp. 22498-22505 ◽  
Author(s):  
Jing Sun ◽  
Yu Zhang ◽  
Chao-Guo Yan
Keyword(s):  
Amino Acid ◽  
Aromatic Aldehydes ◽  
Ethyl Esters ◽  
Efficient Synthesis ◽  
One Pot ◽  
The One

The one-pot four-component reaction of aromatic aldehydes, malononitrile, 1,3-thiazolidinedione and ethyl glycinate hydrochloride in ethanol in the presence of triethylamine afforded trans-dihydrothiophene.

Efficient pseudo five-component synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives promoted by a novel ionic liquid catalyst

2018 ◽  
Vol 73 (3-4) ◽  
pp. 191-195 ◽  
Author(s):  
Zahra Abshirini ◽  
Abdolkarim Zare
Keyword(s):  
Ionic Liquid ◽  
Disulfonic Acid ◽  
Thermal Gravimetric ◽  
One Pot ◽  
Mild Conditions ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
The One ◽  
C Nmr

AbstractIn this research, initial production and characterization of a novel Brønsted-acidic ionic liquid, namely,N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate ([TMEDSA][HSO4]2), has been described (characterization was achieved using Fourier-transform infrared spectroscopy,1H nuclear magnetic resonance (NMR),13C NMR, and mass and thermal gravimetric spectra). Thereafter, utilization of [TMEDSA][HSO4]2as a highly effectual catalyst for the synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives through the one-pot pseudo five-component reaction of phenylhydrazine (2 eq.) with ethyl acetoacetate (2 eq.) and arylaldehydes (1 eq.) in relatively mild conditions, has been reported.

One-pot synthesis of 3-aminofurans using a simple and efficient recyclable CuI/[bmim]PF6 system

2021 ◽  
Author(s):  
Guguloth Veeranna ◽  
Ramesh Balaboina ◽  
Narasimha Swamy Thirukovela ◽  
Ravindhar Vadde
Keyword(s):  
Secondary Amines ◽  
Terminal Alkynes ◽  
One Pot ◽  
One Pot Synthesis ◽  
System P ◽  
Three Component Reaction ◽  
The One

The one-pot three-component reaction of several 2-ketoaldehdyes, secondary amines and terminal alkynes to access 3-aminofurans was proceeded well in [bmim][PF6] using a simple and cheap CuI catalyst. The resulted 3-aminofuran...

Intermetallic Ni2Si/SiCN as a highly efficient catalyst for the one-pot tandem synthesis of imines and secondary amines

2020 ◽  
Vol 7 (1) ◽  
pp. 82-90 ◽  
Author(s):  
Xiao Chen ◽  
Shuhua Han ◽  
Dongdong Yin ◽  
Changhai Liang
Keyword(s):  
High Activity ◽  
Aromatic Amine ◽  
Reductive Amination ◽  
High Selectivity ◽  
Secondary Amines ◽  
One Pot ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
The One ◽  
Tandem Synthesis

For the one-pot reductive amination of benzaldehyde with nitrobenzene, intermetallic Ni2Si/SiCN from the decomposition of a nickel-modified polysilazane precursor exhibited high activity (>99%) and high selectivity (92% to aromatic amine).

One-pot, chemoselective synthesis of secondary amines from aryl nitriles using a PdPt–Fe3O4 nanoparticle catalyst

2020 ◽  
Vol 10 (13) ◽  
pp. 4201-4209
Author(s):  
Jin Hee Cho ◽  
Sangmoon Byun ◽  
Ahra Cho ◽  
B. Moon Kim
Keyword(s):  
Reductive Amination ◽  
Secondary Amines ◽  
Fe3o4 Nanoparticle ◽  
Catalytic Method ◽  
One Pot ◽  
Chemoselective Synthesis ◽  
Aryl Nitriles ◽  
The One ◽  
Nanoparticle Catalyst

We have developed a new catalytic method for the one-pot, cascade synthesis of unsymmetrical secondary amines via the reductive amination of aryl nitriles with nitroalkanes using a PdPt–Fe3O4 nanoparticle (NP) catalyst.

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