26928-26-7

Upstream product

• 628-71-7 1-Heptyne 
• 402490-62-4 1-bromo-1-fluoro-2-(4-methoxy-phenyl)-ethylene 
• 536-74-3 phenylacetylene 
• 123-11-5 4-methoxy-benzaldehyde 
• 1338228-99-1 (E)-[1-fluoro-2-(4-methoxyphenyl)vinyl]methyldiphenylsilane 
• 637-69-4 4-Methoxystyrene 
• 1608-24-8 3-(2,2-difluoroethenyl)anisole 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 2366-31-6 (Z)-1-bromo-2-fluoroethylene 
• 26928-12-1 (Z)-2-fluoro-3-(4-methoxyphenyl)-2-propenoic acid 
• 26927-88-8 (Z)-3-(4-methoxyphenyl)-2-fluoroacrylic acid ethyl ester 
• 75-69-4 trichlorofluoromethane 

Downstream Products

• 1657-53-0 cis-4-methoxystilbene 
• 1694-19-5 E-1-(phenyl)-2-(4'-methoxyphenyl)ethene 
• 7642-16-2 (Z)-1-methoxy-4-(pent-1-en-1-yl)benzene 
• 18657-10-8 (E)-1-methoxy-4-(pent-1-en-1-yl)benzene 
• 103786-20-5 (E)-1-methoxy-4-(3-methyl-but-1-en-1-yl)benzene 
• 103786-19-2 (Z)-1-methoxy-4-(3-methylbut-1-en-1-yl)benzene 
• 79958-53-5 (E)-1-(3,3-dimethylbut-1-en-1-yl)-4-methoxybenzene 

Relevant academic research and scientific papers

Iron-Catalyzed Regioselective Alkenylboration of Olefins

The first examples of an iron-catalyzed three-component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene-containing substrates, ring cleavage leading to trisubstituted E-alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.

Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of gem-Difluoroalkenes with Water

A copper catalytic system was established for the stereoselective hydrodefluorination of gem-difluoroalkenes through C?F activation to synthesize various Z fluoroalkenes. H2O is used as the hydrogen source for the fluorine acceptor moiety. This mild catalytic system shows good-functional group compatibility, accepting a range of carbonyls as precursors to the gem-difluoroalkenes, including aliphatic, aromatic, and α,β-unsaturated aldehydes and even ketones. It serves as a powerful synthetic method for the late-stage modification of complex compounds.

Stereodivergent hydrodefluorination of: Gem -difluoroalkenes: Selective synthesis of (Z)- and (E)-monofluoroalkenes

We have developed a novel approach for the stereodivergent hydrodefluorination of gem-difluoroalkenes using copper(i) catalysts to obtain stereodefined monofluoroalkenes. Both (Z)- and (E)-terminal monofluoroalkenes were obtained by the hydrodefluorination of gem-difluoroalkenes in the presence of copper(i) catalysts and diboron or hydrosilane, respectively, with high stereoselectivity. DFT calculations were conducted to elucidate the stereoselectivity.

Cu-Catalyzed Stereoselective Borylation of gem-Difluoroalkenes with B2pin2

A novel and efficient method for the synthesis of (Z)-fluorinated alkenylboronic acid pinacol esters via Cu-catalyzed stereoselective borylation of gem-difluoroalkenes using bis(pinacolato)diboron (B2pin2) as the boron source with the assistance of NaOtBu and Xantphos at room temperature was developed.

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.

Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis

Olefin metathesis has had a large impact on modern organic chemistry, but important shortcomings remain: for example, the lack of efficient processes that can be used to generate acyclic alkenyl halides. Halo-substituted ruthenium carbene complexes decompose rapidly or deliver low activity and/or minimal stereoselectivity, and our understanding of the corresponding high-oxidation-state systems is limited. Here we show that previously unknown halo-substituted molybdenum alkylidene species are exceptionally reactive and are able to participate in high-yielding olefin metathesis reactions that afford acyclic 1,2-disubstituted Z-alkenyl halides. Transformations are promoted by small amounts of a catalyst that is generated in situ and used with unpurified, commercially available and easy-to-handle liquid 1,2-dihaloethene reagents, and proceed to high conversion at ambient temperature within four hours. We obtain many alkenyl chlorides, bromides and fluorides in up to 91 per cent yield and complete Z selectivity. This method can be used to synthesize biologically active compounds readily and to perform site- and stereoselective fluorination of complex organic molecules.

Synthesis of monofluoroalkenes through selective hydrodefluorination of gem-difluoroalkenes with Red-Al

A novel and practical approach for the selective hydrodefluorination of gem-difluoroalkenes using Red-Al as a reductant at room temperature in CH2Cl2 without any additional base and metal catalyst was reported. Various monofluoroalkenes were obtained in moderate to high yields with good E-selectivity.

Direct fluorination of styrenes

We have developed a practical method to synthesize fluorostyrene compounds. A mild and regioselective mono-fluorination reaction occurred smoothly for various di- and trisubstituted styrenes in the presence of RuCl3 and N-fluorobenzenesulfonimide (NFSI). A tandem alkyne hydroarylation-olefin fluorination reaction was also developed using an Au catalyst.

Pd-and Cu-catalyzed stereo-and regiocontrolled decarboxylative/C-H fluoroalkenylation of heteroarenes

Pd/Cu-catalyzed decarboxylative/direct C-H alkenylations of heteroarenes with α-fluoroacrylic acid is reported. This method offers step-economical and stereocontrolled access to valuable heteroarylated monofluoroalkenes as both Z and E isomers, which are known to be useful in the synthesis of fluorinated biomolecules.