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Usage

Uses

Used in Pharmaceutical Industry:
Potassium cyclopropyltrifluoroborate is used as a reagent for the Suzuki-Miyaura cross-coupling reactions, which are essential in the synthesis of complex organic molecules, including those with pharmaceutical applications. Its stability and versatility make it a preferred choice for these reactions.
Used in Chemical Synthesis:
Potassium cyclopropyltrifluoroborate is used as a boronic acid surrogate in chemical synthesis, particularly for the formation of carbon-carbon bonds. Its stability and reactivity contribute to the efficient synthesis of various organic compounds.
Used in Research and Development:
In the field of research and development, potassium cyclopropyltrifluoroborate is used as a key component in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds. Its involvement in this reaction aids in the development of new compounds and materials with potential applications in various industries.
Used in Material Science:
Potassium cyclopropyltrifluoroborate is used as a precursor in the synthesis of new materials, such as polymers and composites, due to its ability to form stable carbon-carbon bonds through the Suzuki-Miyaura cross-coupling reactions. This contributes to the development of advanced materials with improved properties for various applications.

Upstream product

• 411235-57-9 cyclopropylboronic acid 

Downstream Products

• 1533425-16-9 1,3-dichloro-2-cyclopropyl-5-nitrobenzene 
• 1428576-35-5 tert-butyl 2-(5-cyclopropyl-2-fluorophenyl)-4-(1-methyl-5-(4-(benzyloxycarbonylamino)azepan-1-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate 
• 1466565-78-5 C₂₅H₂₈N₂O₃ 
• 1450622-08-8 2-(6-(4-((6-amino-3-pyridinyl)sulfonyl)phenyl)-5-cyclopropyl-3-pyridinyl)-1,1,1,3,3,3-hexafluoro-2-propanol 
• 1446679-70-4 C₂₆H₂₅F₄N₃O₄ 
• 1437323-81-3 4-(2-cyclopropyl-4-nitrophenoxy)-6,7-dimethoxyquinoline 
• 1433906-38-7 N-[[1-(3-chloro-5-cyclopropyl-2-pyridyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide 
• 1427064-97-8 5-cyclopropyl-6-cyclopropylmethoxy-nicotinic acid 
• 1421250-08-9 2-(5-cyclopropyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(3,3-dimethylpiperidin-1-yl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine 
• 1421253-27-1 4-cyclopropyl-2-hydroxybenzonitrile 
• 1421253-24-8 5-cyclopropyl-2-methylphenyl trifluoromethanesulfonate 
• 1266118-38-0 1-[6-(trans-4-tert-butyl-cyclohexyloxy)-4-cyclopropyl-quinolin-2-ylmethyl]-azetidine-3-carboxylic acid methyl ester 
• 1400698-63-6 ethyl 4-({(1-cyclopropyl-4-methylisoquinolin-3-yl)[4-(trifluoromethoxy)benzyl] amino}sulfonyl)benzoate 
• 1401222-27-2 tert-butyl 4-(1-(4-cyclopropylphenyl)-5-(pyrazolo[1,5-a]pyrimidine-3-carboxamido)-1H-pyrazol-3-yl)piperidine-1-carboxylate 

Relevant academic research and scientific papers

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

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.

1H, 13C, 19Fand 11B NMR spectral reference data of some potassium organotrifluoroborates

Complete 1H, 13C, 19Fand 11B NMR spectral data for 28 potassium organotrifluoroborates are described. The resonance for the carbon bearing the boron atom is described for most of the studied compounds. A modifie