149777-83-3

Usage

Uses

Used in Organic Synthesis:
2-(4-Methoxyphenyl)-vinylboronic acid pinacol ester is used as a reagent in organic synthesis for the Suzuki-Miyaura cross-coupling reaction. This reaction allows for the formation of carbon-carbon bonds, which is crucial for the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(4-Methoxyphenyl)-vinylboronic acid pinacol ester is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity enable the development of new drugs with improved properties and therapeutic effects.
Used in Agrochemical Industry:
2-(4-Methoxyphenyl)-vinylboronic acid pinacol ester is also utilized in the agrochemical industry for the preparation of agrochemicals. Its application in this field contributes to the development of new pesticides, herbicides, and other agricultural chemicals that can enhance crop protection and yield.

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 75927-49-0 pinacol vinylboronate 
• 637-69-4 4-Methoxystyrene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 768-60-5 4-methoxyphenylacetylen 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 1000163-40-5 S-ethyl (2E)-3-(4-methoxyphenyl)prop-2-enethioate 
• 15197-86-1 1-(2-fluorovinyl)-4-methoxybenzene 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 696-62-8 para-iodoanisole 
• 1430803-71-6 (Z)-2-(2-(4-methoxyphenyl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 99865-39-1 p-Methoxystyryl Acetate 

Downstream Products

• 72316-18-8 (E)-2-(4-methoxyphenyl)vinylboronic acid 
• 1618099-65-2 2-((E)-3-(4-methoxyphenyl)-1-morpholinoallyl)phenol 
• 6303-59-9 (Z)-1-bromo-2-(4-methoxyphenyl)ethene 
• 6303-59-9 (E)-4-(2-bromo-vinyl)-anisole 
• 136618-41-2 E-2'-p-methoxystyryl iodide 

Relevant academic research and scientific papers

Polyhedral Cu2O Crystals for Diverse Aryl Alkyne Hydroboration Reactions

Cu2O cubes, octahedra, and rhombic dodecahedra have been used to examine facet-dependent catalytic activity in aryl alkyne hydroboration reactions. Although the reaction can proceed by using ethanol or other alcohols as solvent, the use of 1,4-dioxane gave the best product yield. All particle shapes gave exclusively the E-product, but the rhombic dodecahedra exposing {110} surfaces were consistently far more reactive than the other particle morphologies. A product yield of 99 % was achieved by using Cu2O rhombic dodecahedra to catalyze the hydroboration of phenylacetylene at 60 °C for 5 h. The rhombic dodecahedra have been shown to catalyze a variety of substituted aryl alkynes, which demonstrates their potential as a versatile catalyst.

Solvent- and metal-free hydroboration of alkynes under microwave irradiation

Boronic esters are versatile building blocks extensively used in organic chemistry and essential to a variety of coupling reactions. In this work, the hydroboration reactions of alkynes were performed without metal catalysts using concomitant microwave ir

Aluminum Hydride Catalyzed Hydroboration of Alkynes

An aluminum-catalyzed hydroboration of alkynes using either the commercially available aluminum hydride DIBAL-H or bench-stable Et3Al?DABCO as the catalyst and H-Bpin as both the boron reagent and stoichiometric hydride source has been developed. Mechanistic studies revealed a unique mode of reactivity in which the reaction is proposed to proceed through hydroalumination and σ-bond metathesis between the resultant alkenyl aluminum species and HBpin, which acts to drive turnover of the catalytic cycle.

Heck versus Suzuki palladium catalysed cross-coupling of a vinylboronate ester with aryl halides

Palladium(O) catalysed cross-coupling of a vinylboronate 1, protected as its' pinacol ester, with aryl halides provides a mixture of the styryl boronates 2 and the styrenes 3 depending upon the reaction conditions.

Photoswitchable metal-mediated catalysis: Remotely tuned alkene and alkyne hydroborations

A photochromic dithienylethene-annulated N-heterocyclic carbene (NHC)-Rh(I) complex was synthesized and found to undergo reversible electrocyclic ring closure upon alternate exposure to UV (λirr 313 nm) and visible (λirr >500 nm) radiation. Under ambient light, the Rh catalyst efficiently promoted the hydroboration of alkenes and alkynes with pinacolborane. However, upon UV irradiation to effect a photocyclization within the NHC ligand, the catalytic activity was reduced by up to an order of magnitude. The disparity in the rates was used to photoswitch the rates of a series of hydroboration reactions, thus demonstrating the first examples of photomodulating a transition-metal catalyst by tuning its electronic properties. The rate attenuation observed under UV irradiation was attributed to inhibition of the rate-determining reductive elimination step arising from a decrease in electron-donating ability of the photocyclized NHC ligated to the Rh center.

An efficient synthesis of chalcones based on the Suzuki reaction

A general method for the synthesis of chalcones based on the Suzuki reaction either between cinnamoyl chlorides and phenylboronic acids or between benzoyl chlorides and phenylvinylboronic acids is described.

Zwitterion-Initiated Hydroboration of Alkynes and Styrene

The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C6F5)3) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C6F5)3) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3. (Figure presented.).

Neosilyllithium-Catalyzed Hydroboration of Alkynes and Alkenes in the Presence of Pinacolborane (HBpin)

We report here a novel protocol for the hydroboration of alkynes and alkenes, which in the presence of neosilyllithium (LiCH2SiMe3) (5 mol %) and pinacolborane efficiently results in the formation of corresponding alkenyl and alkyl b

Synthesis of Acrylonitriles via Mild Base Promoted Tandem Nucleophilic Substitution-Isomerization of α-Cyanohydrin Methanesulfonates

Main observation and conclusion: We have developed an efficient synthesis of acrylonitriles via mild base promoted tandem nucleophilic substitution-isomerization of α-cyanohydrin methanesulfonates with alkenylboronic acids. This transition metal-free protocol works under simple and mild conditions and offers good chemical yields for a wide range of substrates and demonstrates good functional group tolerance. (Figure presented.).

Cobalt-Catalyzed Markovnikov-Type Selective Hydroboration of Terminal Alkynes

A cobalt-catalyzed Markovnikov-type hydroboration of terminal alkynes with HBpin to access α-alkenyl boronates with good regioselectivity and atom economy is reported. A new ligand has been developed for the cobalt hydride catalyst that has been used for a unique Markovnikov selective insertion of terminal alkynes into metal hydride bond. This operationally simple protocol exhibits excellent functional group tolerance to deliver valuable alkene derivatives.