201852-49-5

Usage

Uses

Used in Organic Synthesis:
POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used as a reactant for various organic synthesis applications, including:
1. Suzuki-Miyaura Cross-Coupling:
POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used as a reactant in Suzuki-Miyaura cross-coupling reactions, which are widely employed for the formation of carbon-carbon bonds in organic synthesis.
2. Enantioselective Total Synthesis of Naseseazines A and B:
In the enantioselective total synthesis of naseseazines A and B, POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used for regioselective Friedel-Crafts based arylative dimerization, contributing to the formation of the desired chiral compounds.
3. Metal-Free Chlorodeboronation Reactions:
POTASSIUM BETA-STYRYLTRIFLUOROBORATE is utilized in metal-free chlorodeboronation reactions, which are important for the synthesis of various organic compounds without the need for metal catalysts.
4. Preparation of Aryl Ketones:
In the preparation of aryl ketones, POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used as a reactant in Lewis acid-catalyzed nucleophilic substitution reactions, enabling the formation of aryl ketones from aryl halides and metal enolates.
5. Preparation of Weinreb Amides:
POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used in the preparation of Weinreb amides through palladium-catalyzed cross-coupling reactions, which are valuable intermediates in organic synthesis and have applications in the synthesis of various pharmaceuticals and agrochemicals.

InChI:InChI=1/C8H7BF3.K/c10-9(11,12)7-6-8-4-2-1-3-5-8;/h1-7H;/q-1;+1/b7-6+;

Upstream product

• 1279123-63-5 potassium hydrogenfluoride 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 100-42-5 styrene 
• 4363-35-3 Dihydroxy-styryl-boran 
• 536-74-3 phenylacetylene 

Downstream Products

• 1694-19-5 E-1-(phenyl)-2-(4'-methoxyphenyl)ethene 
• 1152-30-3 (E)-ethyl 4-styrylbenzoate 
• 3783-65-1 (E)-2-(2-phenylethenyl)thiophene 
• 78347-97-4 (E)-3-styrylthiophene 
• 84645-64-7 trans-2-(β-phenylvinyl)thiazole 
• 2633-06-9 (E)-3-(2-phenylvinyl)pyridine 
• 35782-34-4 trans-5-(β-phenylvinyl)pyrimidine 
• 125972-78-3 trans-2-acetyl-5-(β-phenylvinyl)thiophene 
• 538-49-8 2-[(E)-2-phenylethenyl]pyridine 
• 42599-24-6 E-styryl iodide 
• 26057-47-6 (E,E)-1,5-diphenyl-1,4-pentadiene 
• 4714-21-0 4-methylstilbene 
• 3112-03-6 4-acetylstilbene 
• 879413-58-8 methyl 5-(trimethylsilylethynyl)-2-E-(2-phenylethynyl)benzoate 

Relevant academic research and scientific papers

Facile synthesis of iodonium salts by reaction of organotrifluoroborates with p-iodotoluene difluoride

A simple and easy method for the synthesis of various iodonium salts was developed, and involves the reaction of potassium organotrifluoroborates with p-iodotoluene difluoride under mild conditions. The one-pot synthesis of a (Z)-(2-fluoroalkenyl)iodonium

The no-carrier-added synthesis of bromine-76 labeled alkenyl and alkynyl bromides using organotrifluoroborates

A straightforward radiobromination procedure has been developed for the construction of radiobrominated alkenyl and alkynyl bromides. The organotrifluoroborates used as the reactive intermediates are unique in that they are quite polar and thus readily separated from the desired products. Copyright

Stereoselective Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates with alkenyl bromides

The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or

Pd-Catalyzed coupling of benzyl bromides with BMIDA-substituted: N -tosylhydrazones: synthesis of trans -alkenyl MIDA boronates

A palladium-catalyzed stereoselective synthesis of alkenyl boronates from N-methyliminodiacetyl boronate (BMIDA)-substituted N-tosylhydrazone and benzyl bromides is developed. A range of trans-alkenyl MIDA boronates as single stereoisomers were obtained in moderate yields with good functional group compatibility. The resultant boronate products may be transformed to other boron-containing compounds and may also be directly used in cross-coupling reactions.

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.

Catalyst-free and solvent-free hydroboration of alkynes

The hydroboration of alkynes with pinacolborane (HBpin) under catalyst- and solvent-free conditions was demonstrated. Various alkynes were smoothly converted into alkenyl boronate esters in good to excellent yields at 110 °C. The gram-scale hydroboration

H2-Acceptorless Dehydrogenative Boration and Transfer Boration of Alkenes Enabled by Zirconium Catalyst

The first example of an efficient and direct dehydrogenative boration of alkenes for vinyl boronate ester synthesis was achieved using a zirconium catalyst. Our methodology avoids using precious transition metals, additional hydrogen acceptors, high temperatures, and long reaction times, which were required to overcome the reducing ability of borane, to give alkyl boronate esters. Detailed mechanistic studies revealed a reversible reaction pathway and further suggested applying the zirconium complex as a “shuttle catalyst” for transfer boration, which thus sidesteps the use of relatively sensitive borane.

Bifunctional Ligand Enables Efficient Gold-Catalyzed Hydroalkenylation of Propargylic Alcohol

Using the previously designed biphenyl-2-ylphosphine ligand, featuring a remote tertiary amino group, the first gold-catalyzed intermolecular hydroalkenylation of alkynes has been developed. Synthetically valuable conjugated dienyl alcohols are formed in moderate to good yields. A range of alkenyltrifluoroborates are allowed as the alkenyl donor, and no erosion of alkene geometry and/or the propargylic configuration are detected. DFT calculations confirm the critical role of the remote basic group in the ligand as a general-base catalyst for promoting this novel gold catalysis with good efficiency.

A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates

We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.

Highly enantioselective Rh-Catalyzed Alkenylation of imines: Synthesis of Chiral Allylic Amines via Asymmetric addition of Potassium Alkenyltrifluoroborates to N-Tosyl imines

For the first time, simple N-tosyl aryl aldimines, prepared from the condensation of tosyl amide and aromatic aldehydes, can be used as substrates in the rhodium catalyzed 1,2- addition reaction using alkenylboron nucleophiles. In the presence of 1.5 mol % of [RhCl(1e)]2, enantioselective addition of various potassium alkenyltrifluoroborates to aryl aldimines furnished the corresponding chiral allylic amines in 73-96% yield and 72->99.5% ee. Notably, this method efficiently provides the di-, tri-, and tetrasubstituted allylic N-tosyl amines with high asymmetric induction.