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Usage

Uses

Used in Organic Synthesis:
1-(4-Fluorophenyl)vinylboronic Acid, Pinacol Ester is used as a reagent in organic synthesis for the formation of new chemical bonds and the creation of complex molecular structures. Its boronic acid and pinacol ester functionalities enable it to participate in various types of reactions, such as Suzuki-Miyaura cross-coupling, which is widely used for the formation of carbon-carbon bonds.
Used in Chemical Research:
In the field of chemical research, 1-(4-Fluorophenyl)vinylboronic Acid, Pinacol Ester is employed as a research reagent to explore new reaction mechanisms, develop innovative synthetic methods, and investigate the properties of novel compounds. Its unique structure allows researchers to study its reactivity and potential applications in various chemical transformations.
Used in Pharmaceutical Industry:
1-(4-Fluorophenyl)vinylboronic Acid, Pinacol Ester is utilized in the pharmaceutical industry as a building block for the synthesis of bioactive molecules and drug candidates. Its ability to form stable intermediates and participate in various types of reactions makes it a valuable component in the development of new drugs with improved therapeutic properties.
Used in Material Science:
In material science, 1-(4-Fluorophenyl)vinylboronic Acid, Pinacol Ester is employed in the synthesis of advanced materials with unique properties, such as polymers, nanoparticles, and organic-inorganic hybrid materials. Its versatility in forming different types of chemical bonds allows for the creation of materials with tailored characteristics for specific applications, such as sensors, catalysts, and energy storage devices.

InChI:InChI=1/C14H18BFO2/c1-10(11-6-8-12(16)9-7-11)15-17-13(2,3)14(4,5)18-15/h6-9H,1H2,2-5H3

Upstream product

• 766-98-3 1-ethynyl-4-fluorobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 75230-49-8 N′-(1-(4-fluorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 1138077-60-7 2-(1-(4-fluorophenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 54978-50-6 4-cyanophenyl(4-flourophenyl)methanone 
• 345-89-1 4-fluoro-4'-methoxybenzophenone 
• 1301266-96-5 4-fluorophenylvinylboronic acid 
• 1414852-71-3 MIDA ((4-fluorophenyl)oxomethyl)boronate 
• 1449377-22-3 C₁₃H₁₃BFNO₄ 
• 345-83-5 4-fluorobenzophenone 

Relevant academic research and scientific papers

Atroposelective Synthesis of Conjugated Diene-Based Axially Chiral Styrenes via Pd(II)-Catalyzed Thioether-Directed Alkenyl C-H Olefination

The efficient stereoselective synthesis of conjugated dienes, especially those with axial chirality, remains a great challenge. Herein, we report the highly atroposelective synthesis of axially chiral styrenes with a conjugated 1,3-diene scaffold via a Pd(II)-catalyzed thioether-directed alkenyl C-H olefination strategy. This strategy features easy operation, mild reaction conditions, high functional group tolerance (69 examples), complete Z-selectivity, and excellent enantioselectivities (up to 99% ee). Notably, the highly enantioselective synthesis of atropisomers with two stereogenic axes were also achieved using this strategy (up to 99% ee and 97:3 dr). Moreover, the reaction could be scaled up, and the resulting axially chiral styrenes could be easily oxidized into chiral sulfoxide derivatives with high diastereoselectivities, which showed great promise as a new type of sulfur-olefin ligand.

Synthesis of Alkenylboronates from N-Tosylhydrazones through Palladium-Catalyzed Carbene Migratory Insertion

The palladium-catalyzed oxidative borylation reaction of N-tosylhydrazones has been developed. The reaction features mild conditions, broad substrate scope, and good functional group tolerance. It thus represents a highly efficient and practical method for the synthesis of di-, tri-, and tetrasubstituted alkenylboronates from readily available N-tosylhydrazones. One-pot Suzuki coupling and other transformations highlight the synthetic utility of the approach. DFT calculations have revealed that palladium-carbene formation and subsequent boryl migratory insertion are the key steps in the catalytic cycle. The high stereoselectivity observed in the formation of trisubstituted alkenylboronates has been explained by distortion-interaction analysis and NBO analysis.

Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**

Regioselective hydrofunctionalization of alkynes represents a straightforward route to access alkenyl boronate and silane building blocks. In previously reported catalytic systems, high selectivity is achieved with a limited scope of substrates and/or rea

Suzuki coupling of aroyl-MIDA boronate esters – A preliminary report on scope and limitations

Recent methodological reports for synthesizing acyl-MIDA boronate esters compel an investigation of their potential use as substrates in a standard Suzuki-Miyaura cross-coupling reaction. Here we report the production of benzophenones by C[sbnd]C cross coupling between a benzoyl-MIDA boronate ester and a multitude of aryl bromide substrates in adequate yields following optimization under ambient conditions outside of a glove box. Under these standard conditions, none of several acyl-MIDA boronate esters (in an alkyl series) serves as a competent coupling partner. The substrate scope is also limited by the finding that the corresponding trifluoroborates of both acyl- and aroyltrifluroborates are not suitable substrates. For reasons of availability and synthetic difficulty in procuring other aroyl-MIDA boronates, this preliminary study examines the reactivity of benzoyl-MIDA boronate with several aryl bromide substrates.

NOVEL THYROMIMETICS

Compounds are provided having the structure of Formula (I) or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein R1, R2, X1, X2, Y1, and Y2 are as defined herein. Such compounds function as thyromimetics and have utility for treating diseases such as neurodegenerative disorders and fibrotic diseases. Pharmaceutical compositions containing such compounds are also provided, as are methods of their use and preparation.

Reaction Pathways and Redox States in α-Selective Cobalt-Catalyzed Hydroborations of Alkynes

Cobalt(II) alkyl complexes supported by a monoanionic NNN pincer ligand are pre-catalysts for the regioselective hydroboration of terminal alkynes, yielding the Markovnikov products with α:β-(E) ratios of up to 97:3. A cobalt(II) hydride and a cobalt(II) vinyl complex appear to determine the main reaction pathway. In a background reaction the highly reactive hydrido species specifically converts to a coordinatively unsaturated cobalt(I) complex which was found to re-enter the main catalytic cycle.

Rhodium-catalysed diastereo- And enantioselective cyclopropanation of α-boryl styrenes

A rhodium-catalyzed diastereo- and enantio-selective cyclopropanation of a-boryl styrenes with a-diazoarylacetates was established. Rh2(S-PTTL)4 (0.2 mol%) was found to be effective for the conversion, and 21 diastereopure cyclopropylboronates were prepared in high yields with excellent enantioselectivity (ee up to 99%).

Cyclodextrin Cavity-Induced Mechanistic Switch in Copper-Catalyzed Hydroboration

N-heterocyclic carbene-capped cyclodextrin (ICyD) ligands, α-ICyD and β-ICyD derived from α- and β-cyclodextrin, respectively give opposite regioselectivities in a copper-catalyzed hydroboration. The site-selectivity results from two different mechanisms: the conventional parallel one and a new orthogonal mechanism. The shape of the cavity was shown not only to induce a regioselectivity switch but also a mechanistic switch. The scope of interest of the encapsulation of a reactive center is therefore broadened by this study.

Copper-catalyzed regioselective hydroboration of terminal alkynes in aqueous medium

A mild and environment-friendly copper-catalyzed hydroboration of terminal alkynes in aqueous medium was reported. Regioselectivity control was achieved in the presence of cyclodextrin-bispyridine ligand (CD-1). This protocol was successfully applied to inactivated terminal alkynes. Moreover, the ligand was recovered and reused without any loss of activity over five cycles.

Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters

The copper-catalyzed diboration of ketones followed by an acid-catalyzed elimination leads to the formation of 1,1-disubstituted and trisubstituted vinyl boronate esters with moderate to good yields and selectivity. Addition of tosic acid to the crude diboration products provides the corresponding vinyl boronate esters upon elimination. The trisubstituted vinyl boronate esters are formed as the (Z)-olefin isomer, which was established by subjecting the products to a Suzuki-Miyaura coupling reaction to obtain alkenes of known geometry.