850623-36-8

Usage

Uses

Used in Organic Synthesis:
POTASSIUM (4-CYANOPHENYL)TRIFLUOROBORATE is used as a reagent in organic synthesis, particularly in metal-catalyzed cross-coupling reactions, for its ability to facilitate the formation of carbon-carbon and carbon-heteroatom bonds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, POTASSIUM (4-CYANOPHENYL)TRIFLUOROBORATE is used as a key intermediate in the synthesis of various drug molecules, contributing to the development of new therapeutic agents.
Used in Agrochemical Production:
POTASSIUM (4-CYANOPHENYL)TRIFLUOROBORATE is utilized as a building block in the creation of agrochemicals, aiding in the development of effective and environmentally friendly pesticides and other agricultural chemicals.
Used in Functional Materials:
This organoboron compound is employed in the synthesis of functional materials with specific properties, such as conductivity, magnetism, or luminescence, for applications in various high-tech industries.

InChI:InChI=1/C7H4BF3N.K/c9-8(10,11)7-3-1-6(5-12)2-4-7;/h1-4H;/q-1;+1

Upstream product

• 161664-51-3 C₉H₁₀BNO₂ 
• 623-03-0 4-Cyanochlorobenzene 
• 1279123-63-5 potassium hydrogenfluoride 
• 13675-18-8 tetrahydroxydiboron 
• 3058-39-7 4-iodobenzonitrile 
• 171364-82-2 4-cyanophenylboronic acid pinacol ester 
• 7789-23-3 potassium fluoride 
• 126747-14-6 4-cyanophenylboronic acid 
• 623-00-7 4-bromobenzenecarbonitrile 
• 138373-10-1 4-cyanophenyl mesylate 

Downstream Products

• 4110-15-0 2-(4-cyanophenyl)-1H-benzo[d]imidazole 
• 27331-37-9 4-(naphthalen-1-yl)benzonitrile 
• 1260684-53-4 1-benzoyl-5-(4-benzonitrile)-(2S)-isopropyl-2,3-dihydro-4(1H)-pyrimidin-4-one 
• 455-18-5 4-CF₃C₆H₄CN 
• 1350898-41-7 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1-(4'-cyanophenyl)ethene 
• 1350898-35-9 2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-(4''-cyanophenyl)ethene 
• 767-00-0 4-cyanophenol 
• 1033204-03-3 3-(4-cyano-phenyl)-naphthalene-1-carboxylic acid methyl ester 
• 157788-40-4 4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-carbonitrile 
• 10540-31-5 4-cyano-4'-fluorobiphenyl 
• 294648-03-6 4-(pyridine-3-yl)benzonitrile 

Relevant academic research and scientific papers

Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes under Mild Conditions

A chemoselective rhodium-catalyzed borylation has been developed for the preparation of aryl boronate esters. The reaction proceeds under mild conditions with excellent selectivity for C-I bonds in bromoiodoarenes and exhibits broad functional group tolerance. This procedure can act as a complementary approach toward bifunctional arenes along with other metal-catalyzed borylations. Additionally, the reaction's utility in the preparation of monomers for metal-catalyzed cross-coupling polymerization is demonstrated.

Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source

In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

Electrochemical ipso-Thiocyanation of Arylboron Compounds

An operationally simple electrochemical method for the transition-metal-free ipso-thiocyanation of arylboronic acids and aryl trifluoroborates has been developed. The SCN electrophile is generated in situ by anodic oxidation of thiocyanate anions, which avoids formation of salt waste and prevents unwanted side reactions arising from chemical oxidants. The reaction proceeds regiospecifically, and the scope extends to non-activated aromatic systems. (Figure presented.).

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.

Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions

A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.

Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]

Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.

Preparation of organotrifluoroborate salts: Precipitation-driven equilibrium under non-etching conditions

Simple, rapid, and scaleable: In contrast to current procedures using corrosive HF/MF or MHF2 reagents (M=e.g. K), a wide range of trifluoroborates can be rapidly, simply, and safely prepared from MF (M=K, Cs), RCO2H, and a boronic a

Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid

The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.

Suzuki-Miyaura coupling reactions of iodo(difluoroenol) derivatives, fluorinated building blocks accessible at near-ambient temperatures

A recently developed method for the near-ambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1-iodoethene and 2,2-difluoro-1-iodo-1- (2′-methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki-Miyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from i-PrOH to t-BuOH suppressed the pathway to these species and improved coupling yields.

Functionalization of (2S)-Isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4- ones by a Suzuki-Miyaura Cross-Coupling Reaction Using Aryltrifluoroborate Salts: Convenient Enantioselective Preparation of α-Substituted β-Amino Acids

A simple protocol for the Pd(OAc)2-catalyzed cross-coupling reaction of 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones with potassium aryltrifluoroborates was developed. The reaction is performed at 110°C with a ligand-free catalyst. In all cases, complete conversion of the 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-onesand aryltrifluoroborates into the C-C coupling products was observed within 30-360 min. It is noteworthy that a largevariety of groups present in the potassium aryltrifluoroborates (-CF3, -OMe, -SEt, -CN, -CHO, -Cl, -Cbz, -NCbz,-OH, -CO2H) could be tolerated. Hydrogenation of the endocyclic double bonds in the Suzuki-Miyaura products followed by acid hydrolysis afforded highly enantioenrichedα-aryl-substituted β-amino acids. We present a general approach for the synthesis of (2S)-isopropyl-5-aryl-2,3- dihydro-4(H)-pyrimidin-4-ones by Suzuki-Miyaura reaction of aryltrifluoroborate salts with(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones in the presence of a palladium catalyst and a base. The arylated compounds were transformed into enantioenriched α-aryl-substituted β-amino acids. Copyright