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Usage

Uses

Used in Organic Synthesis:
POTASSIUM 3-HYDROXYPHENYLTRIFLUOROBORATE is used as a reagent in Suzuki-Miyaura cross-coupling reactions, which are widely used methods for forming carbon-carbon bonds. This application is crucial for creating new organic compounds in the fields of pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, POTASSIUM 3-HYDROXYPHENYLTRIFLUOROBORATE is used as an intermediate for the synthesis of various drugs. Its unique structure allows for the development of new organic compounds with potential therapeutic applications.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, POTASSIUM 3-HYDROXYPHENYLTRIFLUOROBORATE is utilized as an intermediate for the synthesis of different agrochemicals, contributing to the development of innovative products for agricultural use.

Upstream product

• 87199-18-6 3-hydroxyphenylboronic acid 
• 108-43-0 3-monochlorophenol 
• 847974-10-1 C₈H₁₁BO₃ 
• 626-02-8 3-Iodophenol 
• 591-20-8 3-Bromophenol 

Downstream Products

• 1260684-60-3 1-benzoyl-5-(3-hydroxyphenyl)-(2S)-isopropyl-2,3-dihydro-4(1H)-pyrimidin-4-one 
• 1620108-50-0 5-(3-hydroxyphenyl)thienyl-2-sulfonamide 
• 365426-93-3 4'-(trifluoromethyl)-[1,1'-biphenyl]-3-ol 
• 1237747-77-1 4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-ol 
• 1226980-81-9 C₁₂H₁₂O₂ 
• 1224947-47-0 methyl 8-(benzyloxy)-5-(3-hydroxyphenyl)-2-methylquinoline-7-carboxylate 
• 1017601-66-9 1-benzyl-5-(3-hydroxyphenyl)-2,3-dihydropyridin-4(1H)-one 

Relevant academic research and scientific papers

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.

Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: One step greener

The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me2N) 2B-B(NMe2)2], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better under one set of optimized reaction conditions than the other. Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B 2Pin2), the new method represents a more atom-economical and efficient approach to current borylation methods.

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

A facile one-pot preparation of potassium hydroxyaryl- and (hydroxyalkyl)aryltrifluoroborates

Potassium hydroxyaryl- and (hydroxyalkyl)aryltrifluoroborates have been prepared in a simple one-pot process from the corresponding hydroxy-substituted aryl halides in 51-98% yields through an in situ protection of the free hydroxyl group with τ-BuLi. Also, we successfully performed a microwave-promoted Suzuki-Miyaura cross-coupling reaction of these substrates with aryl- and alkenyl bromides in the presence of 0.5 mol % of Pd(OAc)2 catalyst without ligands.