Brønsted Acid-Catalysed Allylic Amination of 1-(2-Aminoaryl)prop-2-en-1-ols to 1,2-Dihydroquinolines

2018 ◽  
Vol 71 (9) ◽  
pp. 673 ◽  
Author(s):  
David Philip Day ◽  
Stuart Adam Henry ◽  
Yichao Zhao ◽  
Jianwen Jin ◽  
Guy James Clarkson ◽  
...  
Keyword(s):  
Room Temperature ◽  
Trifluoromethanesulfonic Acid ◽  
Catalyst Loading ◽  
Synthetic Method ◽  
Bronsted Acid ◽  
Allylic Amination ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Brönsted Acid ◽  
Wide Range

A highly efficient synthetic method to prepare 1,2-dihydroquinolines that relies on trifluoromethanesulfonic acid (TfOH)-catalysed allylic amination of 1-(2-aminoaryl)prop-2-en-1-ols is described. Achieved at a catalyst loading of 0.01 mol-% under mild conditions at room temperature, the reaction was found to be robust, with a wide range of substitution patterns tolerated. The corresponding N-heterocyclic adducts were obtained in good to excellent yields of 45–93 %.

Aromatization of C2-C6 Aliphatic Hydrocarbons on Copper-Containing ZSM-5 Zeolites

1992 ◽  
Vol 57 (12) ◽  
pp. 2553-2560
Author(s):  
Zdravka Popova ◽  
Katia Aristirova ◽  
Christo Dimitrov
Keyword(s):  
Copper Content ◽  
Acid Strength ◽  
The State ◽  
Aliphatic Hydrocarbons ◽  
Bronsted Acid ◽  
Ion Formation ◽  
Brönsted Acid ◽  
Wide Range ◽  
Carbenium Ion ◽  
Acid Centers

The aromatization of a wide range of model aliphatic and cycloaliphatic hydrocarbons (ethene, ethane, propene, n-hexane, 1-hexene, methylcyclopentane, cyclohexane, cyclohexene) on copper-containing NaZSM-5 and HZSM-5 zeolites has been investigated. It was established that the degree of aromatization is related to carbenium ion formation and depends on the acid strength and copper content of zeolite. Experiments with copper-containing samples reduced prior to use indicated the possibility to enhance the selectivity to aromatization. The change of the state of Cu2+ ions during catalytic experiments confirmed the assumption about participation of Cu0 simultaneously with the Bronsted acid centers in the dehydrogenation/hydrogenation steps.

Cholinium-amino acid based ionic liquids: a new method of synthesis and physico-chemical characterization

2015 ◽  
Vol 17 (32) ◽  
pp. 20687-20698 ◽  
Author(s):  
Serena De Santis ◽  
Giancarlo Masci ◽  
Francesco Casciotta ◽  
Ruggero Caminiti ◽  
Eleonora Scarpellini ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Amino Acid ◽  
Room Temperature ◽  
Chemical Characterization ◽  
New Method ◽  
Room Temperature Ionic Liquids ◽  
Synthetic Method ◽  
Chemical Structures ◽  
Physico Chemical ◽  
Wide Range

Fourteen cholinium-amino acid based room temperature ionic liquids were prepared using a cleaner synthetic method. Chemicophysical properties were well correlated with the wide range of amino acid chemical structures.

One-Step Conversion of Biomass-Derived Furanics into Aromatics by Brønsted Acid Ionic Liquids at Room Temperature

2018 ◽  
Vol 6 (2) ◽  
pp. 2541-2551 ◽  
Author(s):  
Lingli Ni ◽  
Jiayu Xin ◽  
Kun Jiang ◽  
Lu Chen ◽  
Dongxia Yan ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Room Temperature ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
One Step

Brønsted acid-catalyzed 1,2-fluorine migration with fluoroepoxides

2015 ◽  
Vol 44 (45) ◽  
pp. 19636-19641 ◽  
Author(s):  
Tao Luo ◽  
Rui Zhang ◽  
Xiao Shen ◽  
Wei Zhang ◽  
Chuanfa Ni ◽  
...  
Keyword(s):  
Fluorine Atom ◽  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Atom Economy ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Bronsted Acid Catalysis

An efficient 1,2-fluorine migration reaction was realized under Brønsted acid catalysis in the absence of an external fluorinating source. The high fluorine atom economy and very mild conditions make this reaction a promising protocol for the construction of the C–F bond.

Organic Photoredox Catalytic α-C(sp3)–H Phosphorylation of Saturated Aza-Heterocycles

2021 ◽  
Author(s):  
Ming-Jun Yi ◽  
Teng-Fei Xiao ◽  
Wen-Hui Li ◽  
Yi-Fan Zhang ◽  
Pen-Ji Yan ◽  
...  
Keyword(s):  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Metal Free ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysis

A metal-free C(sp3)–H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Brønsted acid catalysis was established under mild conditions. This protocol provided a straightforward and economic access...

An uncommon use of irradiated flavins: Brønsted acid catalysis

2020 ◽  
Vol 56 (42) ◽  
pp. 5661-5664
Author(s):  
Yukihiro Arakawa ◽  
Tomohiro Mihara ◽  
Hiroki Fujii ◽  
Keiji Minagawa ◽  
Yasushi Imada
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Acid Catalysis ◽  
Light Irradiation ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysis

Visible light irradiation to flavins in the presence of thiols and O2 provides Brønsted acidic species that can be used as efficient catalysts for thioacetalizations and for Mannich-type reactions under non-irradiation and mild conditions.

A Brønsted acid-promoted asymmetric intramolecular allylic amination of alcohols

2018 ◽  
Vol 16 (3) ◽  
pp. 380-383 ◽  
Author(s):  
Jianqiao Zhou ◽  
Hexin Xie
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Allylic Amination ◽  
Amination Reaction ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid

An asymmetric intramolecular allylic amination reaction catalyzed by a chiral Brønsted acid is disclosed, affording biologically intriguing chiral 2-substituted hydroquinolines in up to 90% yield and with up to 93% ee.

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