83947-56-2

Usage

Uses

Used in Oxidative Coupling Reactions:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is used as a reactant for oxidative coupling reactions catalyzed by arene ruthenium complexes. Its reactivity allows for the formation of new carbon-carbon bonds, which are essential in the synthesis of complex organic molecules.
Used in Cycloaddition Reactions:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is also employed in cycloaddition reactions, where it can participate in the formation of cyclic compounds. These reactions are crucial for the synthesis of various pharmaceuticals, agrochemicals, and materials.
Used in the Preparation of Allyl Vinyl Ethers:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is used as a starting material for the preparation of allyl vinyl ethers via Cu-catalyzed coupling with alcohols. These allyl vinyl ethers are valuable intermediates in the synthesis of various organic compounds and polymers.
Used in the Preparation of 5-Vinyl-3-Pyridinecarbonitriles:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is utilized in the synthesis of 5-vinyl-3-pyridinecarbonitriles, which serve as potent protein kinase C theta (PKCθ) inhibitors. These inhibitors are important in the development of drugs targeting various diseases, including cancer and inflammatory conditions.
Used in Diastereoselective Addition to Zincated Hydrazones:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is used in diastereoselective addition reactions to zincated hydrazones. This process allows for the selective formation of specific stereoisomers, which are crucial in the synthesis of enantioselective drugs and agrochemicals.
Used in Stereospecific Trapping of Boron/Zinc Bimetallic Intermediates:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is also employed in the stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles. This reaction is an important step in the synthesis of various chiral compounds and catalysts.
Used in Regioselective and Stereoselective Pd-Catalyzed Chelate-Controlled Intermolecular Oxidative Heck Reactions:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is used in regioselective and stereoselective Pd-catalyzed chelate-controlled intermolecular oxidative Heck reactions. These reactions are essential for the formation of specific carbon-carbon bonds with high selectivity, which is crucial in the synthesis of complex organic molecules and pharmaceuticals.

InChI:InChI=1/C14H19BO2/c1-13(2)14(3,4)17-15(16-13)11-10-12-8-6-5-7-9-12/h5-11H,1-4H3/b11-10+

Upstream product

• 100-42-5 styrene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 536-74-3 phenylacetylene 
• 72824-04-5 4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 6783-04-6 (E)-2-(2'-phenylethenyl)-1,3,2-benzodioxaborole 
• 100-52-7 benzaldehyde 
• 83622-41-7 pinacol dichloromethylboronic ester 
• 73183-34-3 bis(pinacol)diborane 
• 79121-47-4 pinacol 1-iodo-2-phenylethane-1-boronate 
• 74213-43-7 C₁₀H₂₂BO₂Si^(1-) 
• 592-41-6 1-hexene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Downstream Products

• 1240492-43-6 racemic 4,4,5,5-tetramethyl-2-((1S,2S)-2-phenylcyclopropyl)-1,3,2-dioxaborolane 
• 1694-19-5 E-1-(phenyl)-2-(4'-methoxyphenyl)ethene 
• 120823-67-8 tert-butyl (E,E)-5-phenylpenta-2,4-dienoate 
• 201852-50-8 (E)-2-Morpholin-4-yl-4-phenyl-but-3-enoic acid 
• 1048990-13-1 tert-butyl (R,3E,5E)-6-phenylhexa-3,5-dien-2-ylcarbamate 
• 124319-49-9 trans-2(S)-<(tert-butoxycarbonyl)amino>-1,6-diphenyl-3,5-hexadiene 
• 1048990-30-2 C₂₃H₂₇NO₂ 
• 1216847-31-2 8-(2-(phenyl-2-yl)vinyl)-3',5'-O-bis(tert-butyldimethylsilyl)-O₆-(2-trimethylsilylethyl)-2'-deoxyguanosine 
• 1239679-30-1 (E)-1'-(3,4-difluorophenyl)-5'-styrylspiro[[1,3]dioxane-2,3'-indolin]-2'-one 
• 1361582-71-9 7-hexyl-5-phenyl-1-tosyl-2,3,4,5-tetrahydro-1H-indole 
• 1361582-35-5 7-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-phenyl-1-tosyl-2,3,4,5-tetrahydro-1H-indole 
• 1361582-36-6 5,7-diphenyl-1-tosyl-2,3,4,5-tetrahydro-1H-indole 
• 1361582-41-3 6,8-diphenyl-1-tosyl-1,2,3,4,5,6-hexahydroquinoline 

Relevant academic research and scientific papers

Synthesis of tri-substituted vinyl boronates via ruthenium-catalyzed olefin cross-metathesis

Tri-substituted vinyl pinacol boronates are synthesized using cross-metathesis of α-substituted vinyl boronates. The reactions proceed with moderate yields and high Z-selectivity when R1 = methyl. When R1 is larger than a methyl group, yields and Z-selectivity are moderate at best, and the reactions are highly substrate dependent.

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

Selective hydroboration of alkynes via multisite synergistic catalysis by PCN-222(Cu)

Zirconium-based porphyrinic MOFs (PMOFs, MOF = metal-organic framework) have gained considerable attention in the field of electric/thermo/photo-catalysis as heterogeneous single-site catalysts; however, the study on multisite synergistic catalysis of PMO

Highly efficient hydroboration of alkynes catalyzed by porous copper-organic framework under mild conditions

The hydroboration of alkynes is crucial due to the wide applications in organic synthesis, while such reaction is often completed with low turnover frequency (TOF) value and long reaction time. Therefore, it is very important and necessary that the hydrob

Creating High Regioselectivity by Electronic Metal-Support Interaction of a Single-Atomic-Site Catalyst

Ligands are the most commonly used means to control the regioselectivity of organic reactions. It is very important to develop new regioselective control methods for organic synthesis. In this study, we designed and synthesized a single-atomic-site catalyst (SAC), namely, Cu1-TiC, with strong electronic metal-support interaction (EMSI) effects by studying various reaction mechanisms. π cloud back-donation to the alkyne on the metal catalytic intermediate was enhanced during the reaction by using transient electron-rich characteristics. In this way, the reaction achieved highly linear-E-type regioselective conversion of electronically unbiased alkynes and completely avoided the formation of branched isomers (ln:br >100:1, TON up to 612, 3 times higher than previously recorded). The structural elements of the SACs were designed following the requirements of the synthesis mechanism. Every element in the catalyst played an important role in the synthesis mechanism. This demonstrated that the EMSI, which is normally thought to be responsible for the improvement in catalytic efficiency and durability in heterogeneous catalysis, now first shows exciting potential for regulating the regioselectivity in homogeneous catalysis.

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and a

Electrochemical Hydroboration of Alkynes

Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This anodic oxidation performed in an undivided cell allowed the formation of a putative boryl radical, which reacted on the alkyne.

Cs4B4O3F10: First Fluorooxoborate with [BF4] Involving Heteroanionic Units and Extremely Low Melting Point

Herein, a new congruently melting mixed-anion compound Cs4B4O3F10 has been characterized as the first fluorooxoborate with [BF4] involving heteroanionic units. Compound Cs4B4O3F10 possesses two highly fluorinated anionic clusters and therefore its formula can be expressed as Cs3(B3O3F6) ? Cs(BF4). The influence of [BF4] units on micro-symmetry and structural evolution was discussed based on the parent compound. More importantly, Cs4B4O3F10 shows the lowest melting point among all the available borates and thus sets a new record for such system. This work is of great significance to enrich and tailor the structure of borates using perfluorinated [BF4] units.

(Z)-Selective Hydroboration of Terminal Alkynes Catalyzed by a PSP-Pincer Rhodium Complex

A highly (Z)-selective hydroboration of terminal alkynes was achieved using a thioxanthene-based PSP-pincer rhodium catalyst. This hydroboration exhibited good chemoselectivity toward alkynes over carbonyl compounds such as ketones and aldehydes. The mechanistic studies indicated the involvement of rhodium-vinylidene intermediates, and the high (Z)-selectivity could be attributed to the rigid and electron-rich nature of the PSP-rhodium catalyst.

Synthesis method of alkenyl boric acid ester

The invention discloses a synthesis method of alkenyl boric acid ester. The alkenyl boric acid ester compound with a diversified structure is obtained by catalyzing hydroboration of alkyne through rare earth. Particularly, the alkenyl boric acid ester com