20405-77-0

Upstream product

• 100-42-5 styrene 
• 373-91-1 hypofluorous acid trifluoromethyl ester 
• 42599-24-6 E-styryl iodide 
• 100-52-7 benzaldehyde 
• 621-82-9 Cinnamic acid 
• 63073-96-1 potassium cinnamate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 118559-15-2 (E)-β-bromo-β-fluorostyrene 
• 201230-82-2 carbon monoxide 
• 107839-99-6 (2,2-difluoro-1-phenylvinyl)trimethylsilane 
• 591-50-4 iodobenzene 
• 874761-91-8 α-iodo-β,β-difluorostyrene 
• 78782-27-1 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane 
• 6783-05-7 trans-2-phenylvinylboronic acid 

Downstream Products

• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 

Relevant academic research and scientific papers

Effect of Substituants on the Structure of the Vinyl Radical: Calculations and Experiments

Literature reports indicate either a linear or a bent configuration for a-substituted vinyl radicals. In order to get a better insight into this structural question, calculations of the structure of some a-substituted vinyl radicals were conducted by the DFT approach [BLYP/6-31G(d,p) and B3LYP/ 6-311G(2d,2p)]. For vinyl radicals bearing α-type substituents (Me, SH, Cl, OH, F), the bent form is found to be the minimum energy structure; the inversion barrier of the E and Z forms is found to markedly increase as the electronegativity of the group increases. Vinyl radicals bearing π-type substituents (CH=CH2, CHO, CN, C6H5) are found to be linear. The effect of β-substituents is much lower, and the β-fluoro- and β-ethenylvinyl radicals, representative of α- and π-type substituents, are calculated to be bent. Comparison with other literature calculations, obtained by different methods for some similar vinylic radicals, supports our computational results. Experimental support was also sought, with particular regards to the inversion barrier of the bent radicals. Since a very high barrier is calculated for the α-fluorovinyl radical, its inversion rate could be slower than the "sampling" time of a proper chemical reaction. Indeed, the α-fluorovinyl radicals, generated from PhCH=C(F)Br by reaction with Bu3SnH/AIBN, retained the configuration of their precursors in the overall hydrodebromination process.

Copper(I)-Mediated Borofluorination of Alkynes

The electrophilic fluorination of N-heterocyclic carbene (NHC) copper(I) vinyls results in fluoroalkene formation. Alkynes can be converted to cis-(β-fluorovinyl)boronates by a reaction with an (NHC)copper(I) boryl generated in situ, followed by N-fluorobenzenesulfonimide (NFSI). This sequence gives rise to anti-Markovnikov fluorination products from terminal alkynes. Oxidation of a cis-(β-fluorovinyl)trifluoroboronate yields an α-fluoroketone, whereas a palladium-catalyzed Suzuki-Miyaura coupling yields a tetrasubstituted monofluoroalkene.

Decarboxylation and fluorination method for cinnamic acid and derivative thereof

The invention discloses a decarboxylation and fluorination method for cinnamic acid and a derivative thereof. The method comprises the steps that the cinnamic acid or the derivative thereof reacts with 1-chloromethyl-4-fluorophenyl-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroboric acid) salt and an alkali compound in one pot, and the fluorination product (mainly a cis-form structure product) of the cinnamic acid or the derivative thereof is obtained. The method fills in the technical blank on the decarboxylation and fluorination method for carboxylic acid connected with SP2 hybridization carbon atoms in the prior art, and is easy to operate, short in process and high in product yield, and the industrial production requirement is met.

Transition metal free decarboxylative fluorination of cinnamic acids with selectfluor

Herein we report a transition metal free decarboxylative fluorination of cinnamic acids with selectfluor. A range of functionalized cinnamic acid derivatives reacted with 2 equiv. of selectfluor and 4 equiv. of base in hydrophobic solvent and water to afford β-fluorostyrene with good yield and Z-stereoselectivity. Kinetic study was conducted.

Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF

A copper-mediated nucleophilic radiofluorination of aryl- and vinylstannanes with [18F]KF is described. This method is fast, uses commercially available reagents, and is compatible with both electron-rich and electron-deficient arene substrates. This method has been applied to the manual synthesis of a variety of clinically relevant radiotracers including protected [18F]F-phenylalanine and [18F]F-DOPA. In addition, an automated synthesis of [18F]MPPF is demonstrated that delivers a clinically validated dose of 200 ± 20 mCi with a high specific activity of 2400 ± 900 Ci/mmol.

Palladium-Catalyzed Stereoconvergent Formylation of (E/Z)-β-Bromo- β-fluorostyrenes: Straightforward Access to (Z)-α-Fluorocinnamic Aldehydes and (Z)-β-Fluorocinnamic Alcohols

We report here the stereoconvergent formylation of (E/Z)-β-bromo- β-fluorostyrene mixtures with carbon monoxide and sodium formate catalyzed by palladium. Optimization of reaction conditions leads to the corresponding pure (Z)-α-fluorocinnamaldehydes in g

Stereoselective synthesis of both stereoisomers of β-fluorostyrene derivatives from a common intermediate

The stereoselective synthesis of both cis- and trans-β-fluorostyrene derivatives from a common intermediate, (Z)-1-aryl-2-fluoro-1-(trimethylsilyl) ethenes, is described. The trans isomers are obtained by a stereospecific replacement of the silyl group in

Acceleration of alkenyltrimethylsilane fluorination under mild conditions using ultrasound

Alkenyltrimethylsilanes are selectively fluorodesilated to alkenyl fluoride very readily by reaction with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis-tetrafluoroborate (Selectfluor) and N-fluorobenzensulfonimids at room temperature under

Synthesis of monofluoroalkenes via Julia-Kocienski reaction

Monofluoromethyl 3,5-bis(trifluoromethyl)phenyl sulfone 1 was synthesized and employed in Julia-Kocienski fluoroolefination reaction with various ketones and aldehydes. Optimal reaction conditions were found to be the treatment of substrates with KOH or C

Fluorination of boronic acids mediated by silver(I) Triflate

A regiospecific Ag-mediated fluorination reaction of aryl- and alkenylboronic acids and esters Is reported. The fluorination reaction uses commercially available reagents, does not require the addition of exogenous ligands, and can be performed on a multigram scale. This report discloses the first practical reaction sequence from arylboronic acid to aryl fluorides.