14900-39-1

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenylvinylboronic acid is used as a synthetic intermediate for the preparation of enol esters, which are important in the halogenation of alkynes. This application is crucial for the development of new pharmaceutical compounds.
Used in Chemical Synthesis:
1-Phenylvinylboronic acid is used as a reactant in Liebeskind-Srogl cross-coupling, a method for the formation of carbon-carbon bonds. This reaction is essential for the synthesis of complex organic molecules, including those with potential applications in various industries.
Used in Material Science:
1-Phenylvinylboronic acid is used as a building block in the homocoupling of arylboronic acids, which leads to the synthesis of biaryls. Biaryls are important structural elements in many materials, such as liquid crystals and pharmaceuticals.
Used in Organic Synthesis:
1-Phenylvinylboronic acid is used as a component in the iterative cross-coupling of boronate building blocks. This process allows for the stepwise construction of complex molecular structures, which can be applied in various fields, including pharmaceuticals and agrochemicals.
Used in Enantioselective Synthesis:
1-Phenylvinylboronic acid is used as a reactant in enantioselective hydrogenation of hydroxyphenyl styrenes. This reaction is crucial for the synthesis of chiral compounds with specific optical properties, which are valuable in the pharmaceutical and agrochemical industries.
Used in Natural Product Synthesis:
1-Phenylvinylboronic acid is used as a reactant in samarium diiodide-mediated cyclization, which is employed for the synthesis of substituted benzannulated cyclooctanol derivatives. These compounds are found in various natural products and can be used as starting materials for the development of new drugs.
Used in Nucleoside Synthesis:
1-Phenylvinylboronic acid is used as a reactant in Suzuki-Miyaura cross-coupling, a method for the synthesis of C-6-substituted uridine phosphonates. These nucleoside analogs are important in the development of antiviral and anticancer drugs.

InChI:InChI=1/C8H9BO2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-6,10-11H,1H2

Upstream product

• 121-43-7 Trimethyl borate 
• 98-81-7 1-bromovinylbenzene 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 100-42-5 styrene 
• 5419-55-6 Triisopropyl borate 
• 100-52-7 benzaldehyde 
• 13061-96-6 dihydroxy-methyl-borane 
• 143825-84-7 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane 

Downstream Products

• 1884-18-0 di-n-butyl-(α-styrenyl)boronate 
• 143825-84-7 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane 
• 415727-02-5 2-(1-phenylethenyl)-1,3,2-dioxabornane 
• 4333-75-9 1-(4-methoxyphenyl)-1-phenylethene 
• 50431-52-2 1-(2-acetylphenyl)-1-phenylethylene 
• 395-21-1 1-(4-fluorophenyl)-1-phenylethylene 
• 943344-16-9 methyl 6-(2-phenylprop-2-enoyl)-1,2,3,4-tetrahydropyridine-1-carboxylate 
• 851478-20-1 (R,S)-N-trifluoroacetyl-7-methoxy-1-methyl-8-(1-phenyl-vinyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine 
• 15260-65-8 2-(1-phenylvinyl)pyridine 
• 1280188-87-5 C₁₇H₁₃BF₂N₂ 
• 1280188-81-9 8-(1-phenylethyl)boron dipyrromethene 
• 1537172-03-4 (3,3-difluoropenta-1,4-dien-2-yl)benzene 
• 1518-20-3 ethyl trans-2-benzoylcyclopropane-1-carboxylate 
• 15982-18-0 cyclopropanecarboxylic acid-2-benzoyl-ethyl ester 

Relevant academic research and scientific papers

The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes

In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.

Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids

Boronic acids are an increasingly important compound class for many applications, including C-C bond formation reactions, medicinal chemistry, and diagnostics. The deprotection of boronic ester intermediates is frequently a problematic and inefficient step in boronic acid syntheses. We describe an approach that highly facilitates this transformation by leveraging the volatility of methylboronic acid and its diol esters. The method is performed under mild conditions, provides high yields, and eliminates cumbersome and problematic purification steps.

Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols

We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.

Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols

We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: Directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.

Rhodium(III)-Catalyzed Cyclopropanation of Unactivated Olefins Initiated by C-H Activation

We have developed a rhodium(III)-catalyzed cyclopropanation of unactivated olefins initiated by an alkenyl C-H activation. A variety of 1,1-disubstituted olefins undergo efficient cyclopropanation with a slight excess of alkene stoichiometry. A series of mechanistic interrogations implicate a metal carbene as an intermediate.

Intermolecular Carboamination of Unactivated Alkenes

Herein, we report the first example of group transfer radical addition of O-vinylhydroxylamine derivatives onto unactivated alkenes. By utilizing O-vinylhydroxylamine derivatives as both the N- and C-donors, this reaction enables intermolecular carboamination of unactivated alkenes in an atom economical fashion. As the process is initiated through N-radical addition followed by C-transfer, linear carboamination products are afforded. This differs from canonical radical carbofunctionalization of olefins, which typically favors branched product owing to initiation by C-radical addition.

Rh(III)-catalyzed cyclopropanation initiated by C-H activation: Ligand development enables a diastereoselective [2 + 1] annulation of N-enoxyphthalimides and alkenes

N-Enoxyphthalimides undergo a Rh(III)-catalyzed C-H activation initiated cyclopropanation of electron deficient alkenes. The reaction is proposed to proceed via a directed activation of the olefinic C-H bond followed by two migratory insertions, first across the electron-deficient alkene and then by cyclization back onto the enol moiety. A newly designed isopropylcyclopentadienyl ligand drastically improves yield and diastereoselectivity.

Asymmetric hydrogenation of 1-phenylethenylboronic acid and esters for the synthesis of chiral organoboron compounds

The hydrogenation of ethanediol 1-phenylethenylboronic ester was carried out at -20 °C under a hydrogen atmosphere (9 atm) in the presence of [Rh(cod)2]BF4-(R)-BINAP (3 mol%). After alkaline hydrogen peroxide oxidation, the reaction gave 1-phenylethanol with 80% e.e.

Cell adhesion-inhibiting antiinflammatory compounds

Compounds having Formula I are useful for treating inflammation. Also disclosed are pharmaceutical compositions comprising compounds of Formula I, and methods of inhibiting/treating inflammatory diseases in a mammal.