97410-25-8

Upstream product

• 774239-48-4 1-(1-bromoethyl)-4-(methylsulfonyl)benzene 
• 2156-04-9 4-Vinylphenylboronic acid 
• 20277-69-4 sodium methansulfinate 
• 5398-77-6 para-methanesulfonylbenzaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 2554-06-5 2,4,6,8-tetramethyl-2,4,6,8-tetravinyl-cyclotetrasiloxane 
• 98-57-7 4-chlorophenyl methyl sulfone 
• 3466-32-8 4-bromoohenyl methyl sulfone 
• 75927-49-0 pinacol vinylboronate 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2768-02-7 (vinyl)trimethoxylsilane 
• 108-05-4 vinyl acetate 
• 79-10-7 acrylic acid 
• 25888-99-7 1-(4-(methylsulfonyl)phenyl)ethan-1-ol 

Downstream Products

• 137473-27-9 ethyl (2E)-3-[4-(methylsulfonyl)phenyl]acrylate 
• 1196155-98-2 3-(4-(methylsulfonyl)phenyl)propanal 
• 1315568-53-6 1,4-bis[4-(methylsulfonyl)styryl]benzene 

Relevant academic research and scientific papers

Rhenium-Catalyzed Decarboxylative Tri-/Difluoromethylation of Styrenes with Fluorinated Carboxylic Acid-Derived Hypervalent Iodine Reagents

Herein, unprecedented rhenium-catalyzed decarboxylative oxytri-/difluoromethylation and Heck-type trifluoromethylation of styrenes have been developed by using hypervalent iodine(III) reagents derived from cheap, stable, and easy-handling fluorinated carboxylic acids. Mechanistic studies revealed a radical decarboxylative trifluoromethylation pathway occurring in these reactions.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent

A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.

Highly selective electroreductive linear dimerization of electron-deficient vinylarenes

A direct electroreductive dimerization of electron-deficient vinylarenes for the synthesis of 1,4-diarylbutane has been developed using a simple undivided cell with inexpensive carbon electrodes at room temperature. The control and deuterium-labeling experiments of electroreductive dimerization suggest that the hydrogen source comes from the solvent CH3CN. This protocol provides a mild and efficient route for the construction of C–C bond in moderate to good yields with high regioselectivity and broad substrate scope.

Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane

We herein disclose the first Ni-catalyzed Hiyama coupling of aryl halides with vinylsilanes. This protocol uses cheap, nontoxic, and stable vinyltrimethoxysilane as the vinyl donor, proceeds under mild and ligand-free conditions, furnishing a diverse variety of styrene derivatives in high yields with excellent functional group compatibility.

Pd-Catalyzed Synthesis of Vinyl Arenes from Aryl Halides and Acrylic Acid

Acrylic acid is presented as an inexpensive, non-volatile vinylating agent in a palladium-catalyzed decarboxylative vinylation of aryl halides. The reaction proceeds through a Heck reaction of acrylic acid, immediately followed by protodecarboxylation of the cinnamic acid intermediate. The use of the carboxylate group as a deciduous directing group ensures high selectivity for monoarylated products. The vinylation process is generally applicable to diversely substituted substrates. Its utility is shown by the synthesis of drug-like molecules and the gram-scale preparation of key intermediates in drug synthesis.

Pd-Catalyzed Vinylation of Aryl Halides with Inexpensive Organosilicon Reagents Under Mild Conditions

Pd-catalyzed Hiyama vinylation reaction of non-activated aryl chlorides and bromides under mild conditions was developed. The use of efficient vinyl donors and electron-rich sterically hindered phosphine ligands was critical for the success of the reaction. The products of this transformation can be used for Am/Cm separation, an important challenge in nuclear fuel reprocessing. The substituent effect on Am/Cm separating selectivity was also achieved, which could contribute to the development of new chromatographic materials for the separation of Am and Cm.

Enantioselective, Catalytic Vicinal Difluorination of Alkenes

The enantioselective, catalytic vicinal difluorination of alkenes is reported by II/IIII catalysis using a novel, C2-symmetric resorcinol derivative. Catalyst turnover via in situ generation of an ArIIIIF2 species is enabled by Selectfluor oxidation and addition of an inexpensive HF–amine complex. The HF:amine ratio employed in this process provides a handle for regioselective orthogonality as a function of Br?nsted acidity. Selectivity reversal from the 1,1-difluorination pathway (geminal) to the desired 1,2-difluorination (vicinal) is disclosed (>20:1 in both directions). Validation with electron deficient styrenes facilitates generation of chiral bioisosteres of the venerable CF3 unit that is pervasive in drug discovery (20 examples, up to 94:06 e.r.). An achiral variant of the reaction is also presented using p-TolI (up to >95 % yield).

Catalytic Geminal Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres

A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-TolI as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include α-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.

Oxidative alkoxycarbonylation of terminal alkenes with carbazates

A range of terminal alkenes smoothly underwent palladium-catalyzed oxidative alkoxycarbonylation with carbazates under an oxygen atmosphere to afford structurally diverse α,β-unsaturated esters in moderate to good yields with excellent regioselectivity and E selectivity.

A general copper-catalyzed sulfonylation of arylboronic acids

A general copper-catalyzed method for the sulfonylation of arylboronic acids with sulfinate salts is described. A variety of alkyl-aryl, diaryl, and alkyl-heteroaryl sulfones were synthesized in good yield.