683774-32-5

Usage

Uses

Used in Organic Synthesis:
6-((TriMethylsilyl)ethynyl)quinoline is used as a versatile building block for the preparation of various functionalized quinoline derivatives. Its unique structural properties make it a valuable component in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-((TriMethylsilyl)ethynyl)quinoline is used for the development of potential pharmaceutical agents. Its unique structural properties allow for the design and synthesis of novel compounds with potential therapeutic applications.
Used in Material Science:
6-((TriMethylsilyl)ethynyl)quinoline may have applications in material science, where its unique structural properties can be utilized to develop new materials with specific properties.
Used in Biological Imaging Studies:
As a fluorescent probe, 6-((TriMethylsilyl)ethynyl)quinoline can be used in biological imaging studies. Its fluorescent properties allow for the visualization and tracking of biological processes at the molecular level.

Upstream product

• 5332-25-2 6-bromoquinoline 
• 1066-54-2 trimethylsilylacetylene 
• 13327-31-6 6-iodoquinoline 

Downstream Products

• 23395-72-4 quinoline-6-carbonitrile 
• 78593-41-6 6-ethynyl-quinoline 

Relevant academic research and scientific papers

Catalytic Activation of Trimethylsilylacetylenes: A One-Pot Route to Unsymmetrical Acetylenes and Heterocycles

For the synthesis of unsymmetrical acetylenes, a Sonogashira coupling-deprotection-Sonogashira coupling reaction sequence is often used. Removal of protecting groups requires harsh conditions or an excess of difficult to handle and expensive reagents. Herein, we disclose a novel catalytic method for the selective deprotection of trimethylsilylacetylenes in Sonogashira reaction. The reagent hexafluorosilicic acid, an inexpensive nontoxic compound, was used to promote the selective desilylation. This method enables the efficient synthesis of unsymmetric acetylenes with other silylated functional groups present. Further possibilities of the method were explored by synthesis of heterocycles.

Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage

Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).

One-pot synthesis of 1,3-enynes with a CF3 group on the terminal sp2 carbon by an oxidative Sonogashira cross-coupling reaction

Oxidative Sonogashira cross-coupling reactions of (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane with arylacetylene were achieved using silver fluoride and a palladium catalyst, to afford high yields of various 1,3-enynes with a CF3 group on the terminal sp2 carbon. Silver fluoride promoted C-Si bond dissociation and oxidation of palladium, enabling catalytic use of palladium.

Direct synthesis of α-trifluoromethyl ketone from (hetero)arylacetylene: Design, intermediate trapping, and mechanistic investigations

Regioselective addition across the alkynes has been achieved in a silver-catalyzed protocol utilizing Langlois reagent (CF3SO2Na) and molecular O2 to access medicinally active α-trifluoromethyl ketone compounds. This metho

Aerobic oxynitration of alkynes with tBuONO and TEMPO

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.

Synthesis of 1-hetarylethylphosphonates

Previously unknown potentially biologically active diethyl 1-(pyridin-3-yl)-, 1-(quinolin-3-yl)-, and 1-(quinolin-6-yl)ethylphosphonates were synthesized by palladium-catalyzed reduction of the corresponding α,β-unsaturated precursors with ammonium formate. The reduction of diethyl 1-(quinolin-6-yl)ethenylphosphonate was accompanied by formation of diethyl 1-(1,2,3,4-tetrahydroquinolin-6-yl)ethylphosphonate as by-product.

Hydrophosphorylation of terminal alkynes catalyzed by palladium

A series of new 1-aryl-, 1-heteroaryl-, and 1-alkylethenylphosphonates was prepared by hydrophosphorylation of terminal acetylenes catalyzed by palladium. A stable in air complex Pd2(dba)3·CHCl3 was applied as catalyst. The reaction mechanism is discussed.