245432-97-7

Usage

Uses

Used in Organic Synthesis:
2-[(1E)-2-(1-Cyclohexen-1-yl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a reagent in organic synthesis for its ability to facilitate the formation of carbon-carbon and carbon-heteroatom bonds. Its unique structure, which includes a cyclohexene ring and a boron atom, makes it a valuable component in creating complex organic molecules.
Used in Chemical Reactions:
In the field of chemical reactions, 2-[(1E)-2-(1-Cyclohexen-1-yl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a catalyst or intermediate, enhancing the efficiency and selectivity of various reaction pathways. Its presence can promote specific transformations, making it a useful tool for chemists in achieving desired outcomes in their experiments.
Used in Pharmaceutical Industry:
2-[(1E)-2-(1-Cyclohexen-1-yl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a building block in the development of pharmaceutical compounds. Its structural features can be incorporated into drug molecules to impart specific biological activities or to improve pharmacokinetic properties, such as solubility, stability, and bioavailability.
Used in Material Science:
In the realm of material science, 2-[(1E)-2-(1-Cyclohexen-1-yl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be utilized as a component in the synthesis of advanced materials with unique properties. Its incorporation into polymers, for instance, may lead to materials with enhanced mechanical strength, thermal stability, or other desirable characteristics.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 77855-67-5 (E)-2-[2-(Cyclohex-1-en-1-yl)ethenyl]benzo[1,3,2]dioxaborole 
• 931-49-7 1-ethenylcyclohexene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1207295-83-7 (E)-1-(2-(allyloxy)vinyl)cyclohex-1-ene 
• 1227742-17-7 (E)-2-cyclohexenylethenyl but-2-enyl ether 
• 1227742-24-6 (E)-2-cyclohexenylethenyl 2-(trimethylsilyl)ethyl ether 
• 1227742-14-4 (E)-2-cyclohexenylethenyl 2-chloroethyl ether 
• 68394-64-9 1-phenyl-4,5,6,7-tetrahydro-1H-indole 
• 495-48-7 azoxybenzene 

Relevant academic research and scientific papers

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.

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.

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

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

Synthesis method of alkenyl borate

The invention discloses a synthesis method of alkenyl borate, which comprises the following steps: adding an alkyne substance, pinacolborane and a lithium amide catalyst into a reaction vessel filled with an organic solvent in a nitrogen atmosphere, stirring and mixing, uniformly mixing, reacting at the temperature of 70-110 DEG C for 18-28 hours, filtering and purifying after the reaction is finished to obtain a product, wherein the lithium amide catalyst is lithium bis(trimethylsilyl) amide; the alkyne substance is any one of substances such as phenylacetylene and 4-methyl phenylacetylene. The method is mild in reaction condition, easy to achieve and safe; the target product can be directly synthesized, an intermediate product does not need to be separated, and the highest yield can reach 98%; the catalyst is easy to prepare, and reactant raw materials are easy to obtain; the waste solution in the reaction process is less, other pollution gases and liquids are not discharged, so that the discharge of the waste solution is reduced, and the method has the advantages of protecting the environment and guaranteeing the health of operators.

Stereoselective Diels-Alder Reactions of gem-Diborylalkenes: Toward the Synthesis of gem-Diboron-Based Polymers

Although gem-diborylalkenes are known to be among the most valuable reagents in modern organic synthesis, providing a rapid access to a wide array of transformations, including the construction of C-C and C-heteroatom bonds, their use as dienophile-reactive groups has been rare. Herein we report the Diels-Alder (DA) reaction of (unsymmetrical) gem-diborylalkenes. These reactions provide a general and efficient method for the stereoselective conversion of gem-diborylalkenes to rapidly access 1,1-bisborylcyclohexenes. Using the same DA reaction manifold with borylated-dienes and gem-diborylalkenes, we also developed a concise, highly regioselective synthesis of 1,1,2-tris- A nd 1,1,3,4-tetrakis(boronates)cyclohexenes, a family of compounds that currently lack efficient synthetic access. Furthermore, DFT calculations provided insight into the underlying factors that control the chemo-, regio-, and stereoselectivity of these DA reactions. This method also provides stereodivergent syntheses of gem-diborylnorbornenes. The utility of the gem-diborylnorbornene building blocks was demonstrated by ring-opening metathesis polymerization (ROMP), providing a highly modular approach to the first synthesis of the gem-diboron-based polymers. Additionally, these polymers have been successfully submitted to postpolymerization modification reactions. Given its simplicity and versatility, we believe that this novel DA and ROMP approach holds great promise for organoboron synthesis as well as organoboron-based polymers and that it will result in more novel transformations in both academic and industrial research.

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.).

Cobalt-Catalyzed Hydroboration of Terminal and Internal Alkynes

A novel methodology to access synthetically versatile vinylboronic esters through a ligand-controlled cobalt-catalyzed hydroboration of terminal and internal alkynes is reported. The approach relies on the in situ reduction of Co(II) by H-BPin in the presence of bisphosphine ligands generating catalytically active Co(I) hydride complexes. This procedure avoids the use of stoichiometric amounts of base, and no boron-containing byproducts are generated which is translated into high functional group tolerance and atom economy.

Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates

An efficient Cu-catalyzed C-H alkenylation with acyclic and cyclic vinyl boronates was realized for the first time under mild conditions. The scope of the vinyl borons and the compatibility with functional groups including heterocycles are superior than Pd-catalyzed C-H coupling with vinyl borons, providing a reliable access to multisubstituted alkenes and dienes. Subsequent hydrogenation of the product from the internal vinyl borons will lead to installation of secondary alkyls.