446065-11-8

Usage

Uses

Used in Organic Synthesis:
Potassium cyclohexyltrifluoroborate is used as a source of cyclohexyltrifluoroborate for various organic reactions, facilitating the formation of carbon-carbon bonds. Its stability and solvent compatibility make it a preferred reagent in this application.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, potassium cyclohexyltrifluoroborate is used as a key reagent in the synthesis of various drugs. Its ability to form carbon-carbon bonds is crucial for creating complex molecular structures required in medicinal chemistry.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, potassium cyclohexyltrifluoroborate is utilized for the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity in forming carbon-carbon bonds contributes to the development of effective and targeted agrochemical products.
Used in Development of Therapeutic Compounds:
Due to its low toxicity and high tolerance in biological systems, potassium cyclohexyltrifluoroborate is used in the development of new compounds with potential therapeutic applications. Its properties make it a preferred choice for creating molecules that can interact with biological targets safely and effectively.

Upstream product

• 110-83-8 cyclohexene 
• 4441-56-9 cyclohexylboronic acid 
• 1279123-63-5 potassium hydrogenfluoride 
• 87100-15-0 cyclohexylboronic acid pinacol ester 
• 97782-70-2 cyclohexyldiisopropoxyborane 
• 39105-81-2 (dichloro)(cyclohexyl)borane 
• 13675-18-8 tetrahydroxydiboron 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 931-50-0 cyclohexylmagnesium bromide 
• 931-51-1 cyclohexylmagnesiumchloride 
• 110-51-0 borane pyridine 

Downstream Products

• 14049-36-6 chlorotrifluorosilane 
• 18356-71-3 difluoro dichlorosilane 
• 14965-52-7 trichloro fluorosilane 
• 7783-61-1 silicon tetrafluoride 
• 16219-90-2 3-cyclohexylpyridine 
• 2206-48-6 2-cyclohexylanisole 
• 1124-53-4 N-cyclohexylacetamide 
• 108-93-0 cyclohexanol 
• 4441-56-9 cyclohexylboronic acid 
• 1430420-17-9 C₁₉H₂₃N 
• 1430420-18-0 C₁₉H₂₃N 
• 97311-75-6 2-(1-Cyclohexylethyl)-propandisaeure-diethylester 
• 10264-57-0 3-cyclohexyl-1-cyclopentanone 
• 75354-08-4 2-Cyclohexylbutandisaeure-diethylester 

Relevant academic research and scientific papers

Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis

Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C?H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.

Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation

The intermolecular radical addition to the carbonyl group is difficult due to the facile fragmentation of the resulting alkoxyl radical. To date, the intermolecular radical addition to ketones, a valuable approach to construct quaternary carbon centers, remains a formidable synthetic challenge. Here, we report the first visible-light-induced intermolecular alkyl boronic acid addition to α-ketoacids enabled by the Lewis acid activation. The in situ boron complex formation is confirmed by various spectroscopic measurements and mechanistic probing experiments, which facilitates various alkyl boronic acid addition to the carbonyl group and prevents the cleavage of the newly formed C-C bond. Diversely substituted lactates can be synthesized from readily available alkyl boronic acids and ketoacids at room temperature merely under visible light irradiation, without any additional reagent. This boron activation approach can be extended to alkyl dihydropyridines as radical precursors with external boron reagents for primary, secondary, and tertiary alkyl radical additions. The pharmaceutically useful anticholinergic precursors are easily scaled up in multigrams under metal-free conditions in flow reactors.

Selective C?N Borylation of Alkyl Amines Promoted by Lewis Base

An efficient method for the metal-free deaminative borylation of alkylamines, using bis(catecholato)diboron as the boron source, to directly synthesize various alkyl potassium trifluoroborate salts is introduced. The key to this high reactivity is the utilization of pyridinium salt activated alkylamines, with a catalytic amount of a bipyridine-type Lewis base as a promoter. This transformation shows good functional-group compatibility (e.g., it is unimpeded by the presence of a ketone, indole, internal alkene, or unactivated alkyl chloride) and can serve as a powerful synthetic tool for borylation of amine groups in complex compounds. Mechanistic experiments and computations suggest a mechanism in which the Lewis base activated B2cat2 unit intercepts an alkyl radical generated by single-electron transfer (SET) from a boron-based reductant.

Preparation of alkyltrifluoroborates via Matteson Hydroboration Method

An efficient one-pot method for synthesis of simple alkyltrifluoroborate salts has been developed. Alkyldichloroboranes, prepared by the Matteson Hydroboration Method using in situ generated HBCl2, were esterified with 2-propanol, treated with

Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis

The alkynylbenziodoxole derivatives are recently developed alkynylation reagents in organic synthesis, which demonstrate excellent radical alkynylation reactivity in photoredox catalysis reactions. Herein we report the synthesis of alkynylbenziodoxole derivatives with difluoro, monofluoro, monomethoxy, and dimethoxy substitution on the benziodoxole moiety, and investigated their radical alkynylation reactivity for the first time. A series of mechanistic experiments were conducted to study the radical acceptor and oxidative quencher reactivity of alkynylbenziodoxoles, in which unsubstituted alkynylbenziodoxoles played balancing roles in both processes, while electron-rich benziodoxole derivatives demonstrate synthetic advantages in some cases.

Decarboxylative Borylation of Aliphatic Esters under Visible-Light Photoredox Conditions

The conventional methods for preparing alkyl boronates often necessitate anhydrous and demanding reaction conditions. Herein, a new, operationally simple decarboxylative borylation reaction of readily available aliphatic acid derivatives under additive-free visible-light photoredox conditions in nonanhydrous solvents has been described. Primary and secondary alkyl boronates or tetrafluoroborates with various functional groups were prepared accordingly. A catalytic cycle involving alkyl radical reaction with base-activated diboron species has been proposed.

Synergistic Photoredox/Nickel Coupling of Acyl Chlorides with Secondary Alkyltrifluoroborates: Dialkyl Ketone Synthesis

Visible light photoredox/nickel dual catalysis has been employed in the cross-coupling of acyl chlorides with potassium alkyltrifluoroborates. This protocol, based on single-electron-mediated alkyl transfer, circumvents the restriction of using reactive alkylmetallic nucleophiles in transition-metal-catalyzed acylation and achieves a mild and efficient method for the synthesis of unsymmetrical alkyl ketones. In this approach, a variety of acyl chlorides have been successfully coupled with structurally diverse potassium alkyltrifluoroborates, generating the corresponding ketones with good yields.

Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N-C Cleavage of Imides

An electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through N-C(O) bond activation, made possible through the lower activation energy for metal insertion into this bond due to delocalization of the lone pair of electrons on the nitrogen by electron-withdrawing groups. The operationally simple and mild cross-coupling reaction is performed at ambient temperature and exhibits tolerance for a variety of functional groups.

Direct Conversion of Carboxylic Acids to Alkyl Ketones

An efficient and mild method for acyl-Csp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated c