166328-14-9

Usage

Uses

Used in Organic Synthesis:
Potassium 2-furantrifluoroborate is used as a reagent for ether-forming cross-coupling reactions, facilitating the formation of ether linkages in organic molecules.
Used in Oxidation Processes:
In the field of oxidation, Potassium 2-furantrifluoroborate is used as a reagent for oxidation reactions using Oxone, a popular oxidizing agent.
Used in Cross-coupling with Alkyl Electrophiles:
This organotrifluoroborate is also utilized as a reagent in cross-coupling reactions with alkyl electrophiles, allowing for the formation of carbon-carbon bonds in organic synthesis.
Used in Halopurine Synthesis:
Potassium 2-furantriflouroborate is employed as a reagent in cross-coupling with halopurines, which are important building blocks in the synthesis of various biologically active compounds.
Used in Suzuki-Miyaura Reactions:
In the realm of cross-coupling reactions, Potassium 2-furantrifluoroborate is used as a reagent in Suzuki-Miyaura reactions, a widely used method for forming carbon-carbon bonds, particularly in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
Potassium 2-furantrifluoroborate is used as a key intermediate in the synthesis of various pharmaceutical compounds, due to its ability to participate in a wide range of chemical reactions.
Used in Material Science:
In the field of material science, Potassium 2-furantrifluoroborate is used as a building block for the development of new materials with specific properties, such as conductivity or stability, by participating in various cross-coupling reactions.

Upstream product

• 13331-23-2 fur-2-ylboronic acid 
• 7789-23-3 potassium fluoride 
• 1279123-63-5 potassium hydrogenfluoride 

Downstream Products

• 17221-37-3 2-(4-chlorophenyl)furan 
• 55484-03-2 2-(2'-furyl)pyridine 
• 27110-82-3 2-(furan-2-yl)pyrimidine 
• 1101167-53-6 1-(4-(furan-2-yl)phenyl)-1H-pyrrole 
• 17113-31-4 2-(4-methoxyphenyl)furan 
• 38527-54-7 2-(2'-methylphenyl)furan 
• 64468-77-5 2-(4-cyanophenyl)furan 
• 53355-25-2 methyl 4-(2-furanyl)benzoate 
• 69836-64-2 N-(4-furan-2-ylphenyl)acetamide 
• 1101167-52-5 3-(furan-2-yl)-4,5-dimethoxybenzonitrile 
• 60456-77-1 4-furylbenzaldehyde 
• 35216-08-1 2-(4-acetylphenyl)furan 
• 28123-72-0 2-(4-nitrophenyl)furan 
• 13331-23-2 fur-2-ylboronic acid 

Relevant academic research and scientific papers

Refining boron-iodane exchange to access versatile arylation reagents

Aryl(Mes)iodonium salts, which are multifaceted aryl transfer reagents, are synthesized via boron-iodane exchange. Modification to both the nucleophilic (aryl boron) and electrophilic (mesityl-λ3-iodane) reaction components results in improved yield and faster reaction time compared to previous conditions. Mechanistic studies reveal a pathway that is more like transmetallation than SEAr.

Reaction rate differences between organotrifluoroborates and boronic acids in BINOL-catalyzed conjugate addition to enones

Enantioselective organocatalysis has been successfully employed in combination with trifluoroborate reagents for novel organic transformations over the last decade. However, no experimental rate studies of these reactions have been reported. Herein we report Hammett plot analysis of the organocatalyzed enantioselective conjugate addition of alkenyl, aryl, and heteroaryl trifluoroborate salts to chalcone derivatives with substitution at both the β-aryl and keto-aryl positions. The rate trend for keto-aryl substitution diverges from that of boronic acid nucleophiles in that the keto-aryl substituent for trifluoroborate salts does not measurably impact reaction rate in a manner consistent with charge stabilization. In addition, variable temperature NMR in combination with quantitative thin-layer chromatography (TLC) analysis suggests that the reaction is impacted by the low solubility of the trifluoroborate salts, so particle size and stirring speed affect reaction rates.

Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings

Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

Solvent-free double-screw extrusion continuous synthesis method of potassium aryltrifluoroborate

The invention belongs to the technical field of fine chemistry, and more specifically relates to a solvent-free double-screw extrusion continuous synthesis method of potassium aryltrifluoroborate. According to the solvent-free double-screw extrusion continuous synthesis method, arylboronic acid and potassium hydrogen fluoride are subjected to high speed stirring so as to obtain a uniformly mixed material; the uniformly mixed material is continuously introduced into a double screw extruder through a feed inlet, extrusion time is set to be 5 to 10min, the temperature is maintained at room temperature, a solid material obtained via continuous extrusion is collected in a receiving container containing water; stirring dissolving of inorganic salts is carried out so as to obtain a slurry or a suspension liquid; filtering is carried out; an obtained filter cake is subjected to water washing and drying so as to obtain potassium aryltrifluoroborate, and an obtained filtrate is recycled into thereceiving container for recycling. According to the solvent-free double-screw extrusion continuous synthesis method, the double screw extruder is taken as a reactor, solvent-free solid-state reactioncontinuous production is realized, the efficiency is higher than that of a kettle type batch reactor; using of organic solvents is avoided; the aqueous solution of excess and by product inorganic salts can be recycled; the three wastes are reduced; the solvent-free double-screw extrusion continuous synthesis method is clean and is friendly to the environment; production cost is reduce; and industrial application value is high.

Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors

Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series α-substituted tetrahydro-β-carboline (THβC) derivatives were synthesized via T+BF4--mediated oxidative C–H functionalization of N-aryl THβCs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a–b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model.

Organotrifluoroborate hydrolysis: Boronic acid release mechanism and an acid-base paradox in cross-coupling

The hydrolysis of potassium organotrifluoroborate (RBF3K) reagents to the corresponding boronic acids (RB(OH)2) has been studied in the context of their application in Suzuki-Miyaura coupling. The "slow release" strategy in such SM couplings is only viable if there is an appropriate gearing of the hydrolysis rate of the RBF3K reagent with the rate of catalytic turnover. In such cases, the boronic acid RB(OH)2 does not substantially accumulate, thereby minimizing side reactions such as oxidative homocoupling and protodeboronation. The study reveals that the hydrolysis rates (THF, H2O, Cs2CO 3, 55 °C) depend on a number of variables, resulting in complex solvolytic profiles with some RBF3K reagents. For example, those based on p-F-phenyl, naphthyl, furyl, and benzyl moieties are found to require acid catalysis for efficient hydrolysis. This acid-base paradox assures their slow hydrolysis under basic Suzuki-Miyaura coupling conditions. However, partial phase-splitting of the THF/H2O induced by the Cs2CO 3, resulting in a lower pH in the bulk medium, causes the reaction vessel shape, material, size, and stirring rate to have a profound impact on the hydrolysis profile. In contrast, reagents bearing, for example, isopropyl, β-styryl, and anisyl moieties undergo efficient "direct" hydrolysis, resulting in fast release of the boronic acid while reagents bearing, for example, alkynyl or nitrophenyl moieties, hydrolyze extremely slowly. Analysis of B-F bond lengths (DFT) in the intermediate difluoroborane, or the Swain-Lupton resonance parameter (R) of the R group in RBF3K, allows an a priori evaluation of whether an RBF3K reagent will likely engender "fast", "slow", or "very slow" hydrolysis. An exception to this correlation was found with vinyl-BF 3K, this reagent being sufficiently hydrophilic to partition substantially into the predominantly aqueous minor biphase, where it is rapidly hydrolyzed.

Scope of the suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates

A wide variety of bench-stable potassium heteroaryltrifluoroborates were prepared, and general reaction conditions were developed for their cross-coupling to aryl and heteroaryl halides. The cross-coupled products were obtained in good to excellent yields. This method represents an efficient and facile installation of heterocyclic building blocks onto preexisting organic substructures.