75414-02-7

Usage

Derivative of tetrahydroquinoline

8-Fluoro-1,2,3,4-tetrahydroquinoline is a fluorinated derivative of tetrahydroquinoline, a bicyclic nitrogen-containing compound.

Building block

Commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals due to its versatile reactivity.

Fluorine atom

The fluorine atom in the compound provides unique properties for the development of new drugs and agricultural products.

Applications

Has potential applications in the field of organic chemistry and chemical research.

Structure

Interesting and important compound for various scientific and industrial purposes.

Upstream product

• 394-68-3 8-fluoroquinoline 
• 38470-28-9 8-fluoro-2,3-dihydro-1H-quinolin-4-one 

Downstream Products

• 394-68-3 8-fluoroquinoline 

Relevant academic research and scientific papers

Heterogeneous Hydrogenation of Quinoline Derivatives Effected by a Granular Cobalt Catalyst

We communicate a convenient method for the pressure hydrogenation of quinolines in aqueous solution by using a particulate cobalt-based catalyst that is prepared in situ from simple Co(OAc)2 4H2O through reduction with abundant zinc powder. This catalytic protocol permits a brisk and atom-efficient access to a variety of 1,2,3,4-tetrahydroquinolines thereby relying solely on easy-to-handle reagents that are all readily obtained from commercial sources. Both the reaction setup assembly and the autoclave charging procedure are conducted on the bench outside an inert-gas-operated containment system, thus rendering the overall synthesis time-saving and operationally very simple.

Utilization of renewable formic acid from lignocellulosic biomass for the selective hydrogenation and/or N-methylation

Lignocellulosic biomass is one of the most abundant renewable sources in nature. Herein, we have developed the utilization of renewable formic acid from lignocellulosic biomass as a hydrogen source and a carbon source for the selective hydrogenation and further N-methylation of various quinolines and the derivatives, various indoles under mild conditions in high efficiencies. N-methylation of various anilines is also developed. Mechanistic studies indicate that the hydrogenation occurs via a transfer hydrogenation pathway.

Homogeneous pressure hydrogenation of quinolines effected by a bench-stable tungsten-based pre-catalyst

We report on an operationally simple catalytic method for the tungsten-catalyzed hydrogenation of quinolines through the use of the easily handled and self-contained precursor [WCl(η5-Cp)(CO)3]. This half sandwich complex is indefinitely storable on the bench in simple screw-capped bottles or stoppered flasks and can, if required, be prepared on a multi-gram scale while the actual catalytic transformations were performed in the presence of a Lewis acid in order to achieve both decent substrate conversions and product yields. The described method represents a facile and atom-efficient access to a variety of 1,2,3,4-tetrahydroquinolines that circumvents the use of cost-intensive and oxygen-sensitive phosphine ligands as well as auxiliary hydride reagents.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Cu-Catalyzed Chemoselective Reduction of N-Heteroaromatics with NH3·BH3 in Aqueous Solution

An efficient catalytic system was successfully developed on reduction of N-heteroaromatics with H3N?BH3 as hydrogen source in CuSO4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH-, NH2-, Cl-, Br-, etc., contained quinolines, quinoxalines, 1,5-naphthyridines and quinazolines were all reduced smoothly. Mechanistic studies suggested that [Cu-H] intermediate might be generated from NH3?BH3, which was believed to form with H3N?BH3 in CuSO4 solution.

Convenient synthesis of cobalt nanoparticles for the hydrogenation of quinolines in water

Easily accessible cobalt nanoparticles are prepared by hydrolysis of NaBH4 in the presence of inexpensive Co(ii) salts. The resulting material is an efficient catalyst for the hydrogenation of quinoline derivatives in water. The activity and chemoselectivity of this catalyst are comparable to other cobalt-based heterogeneous catalysts.

Homogeneous Hydrogenation with a Cobalt/Tetraphosphine Catalyst: A Superior Hydride Donor for Polar Double Bonds and N-Heteroarenes

The development of catalysts based on earth abundant metals in place of noble metals is becoming a central topic of catalysis. We herein report a cobalt/tetraphosphine complex-catalyzed homogeneous hydrogenation of polar unsaturated compounds using an air- and moisture-stable and scalable precatalyst. By activation with potassium hydroxide, this cobalt system shows both high efficiency (up to 24 000 TON and 12 000 h-1 TOF) and excellent chemoselectivities with various aldehydes, ketones, imines, and even N-heteroarenes. The preference for 1,2-reduction over 1,4-reduction makes this method an efficient way to prepare allylic alcohols and amines. Meanwhile, efficient hydrogenation of the challenging N-heteroarenes is also furnished with excellent functional group tolerance. Mechanistic studies and control experiments demonstrated that a CoIH complex functions as a strong hydride donor in the catalytic cycle. Each cobalt intermediate on the catalytic cycle was characterized, and a plausible outer-sphere mechanism was proposed. Noteworthy, external inorganic base plays multiple roles in this reaction and functions in almost every step of the catalytic cycle.

General and Chemoselective Copper Oxide Catalysts for Hydrogenation Reactions

Copper oxide catalysts have been prepared by pyrolysis of copper acetate on aluminum oxide. The material resulting from pyrolysis at 800 °C allows for catalytic hydrogenations at low temperature of a variety of unsaturated compounds such as quinolines, alkynes, ketones, imines, and polycyclic aromatic hydrocarbons as well as nitroarenes with good activity and selectivity.

Iodine catalyzed reduction of quinolines under mild reaction conditions

A reduction of quinolines to synthetically versatile tetrahydroquinoline molecules with I2 and HBpin is described. In the presence of iodine (20 mol%) as a catalyst, reduction of quinolines and other N-heteroarenes proceeded readily with hydroboranes as the reducing reagents. The broad functional-group tolerance, good yields and mild reaction conditions imply high practical utility.

Synthesis method of 1, 2, 3, 4-tetrahydroquinoline compound

Belonging to the technical field of organic chemical synthesis, the invention discloses a synthesis method of a 1, 2, 3, 4-tetrahydroquinoline compound. The method adopts elemental iodine as the catalyst, uses borane as the reductant, and subjects a quinoline compound to catalytic reduction reaction, thus obtaining the product. Compared with the existing synthesis methods, the method has the greatest characteristics of use of cheap I2 as the catalyst, no need for metal to participate in reaction, mild reaction conditions, rapidity and high efficiency, high catalytic efficiency, simple operation, good selectivity, high product conversion rate up to 80% or more, is of great popularization and application value, and is beneficial to industrial production.