251928-76-4

Usage

Boron-containing compound

The compound contains a boron atom, which is a key feature for its use in organic synthesis reactions.

Cyclohexylvinyl group

A vinyl group (carbon-carbon double bond) attached to a cyclohexane ring, which allows for the formation of carbon-carbon bonds.

Tetramethyl-1,3,2-dioxaborolane moiety

A boron-containing ring structure with four methyl groups (carbon-hydrogen groups) attached to it, which provides stability and reactivity to the compound.

Commonly used as a boron source in organic synthesis

The compound is often utilized as a source of boron in the synthesis of organic compounds.

Used in cross-coupling reactions

The compound is often used in reactions such as Suzuki-Miyaura and Stille couplings, which are used to form carbon-carbon bonds.

Facilitates the construction of complex organic molecules

The compound aids in the formation of complex organic molecules by providing a source of boron.

Valuable precursor for creating functionalized organic compounds

The presence of the boron atom in the compound makes it a useful starting material for the synthesis of a wide range of functionalized organic compounds.

Applications in pharmaceuticals, agrochemicals, and materials science

The compound has a wide range of potential uses in various fields, including the production of drugs, pesticides, and other materials.

Upstream product

• 5664-20-0 vinylidenecyclohexane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 87100-15-0 cyclohexylboronic acid pinacol ester 
• 931-48-6 2-cyclohexylacetylene 
• 73183-34-3 bis(pinacol)diborane 
• 16722-09-1 trimethylsilyloxirane 
• 52470-92-5 1,1-Dibromomethylcyclohexane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 75-11-6 diiodomethane 
• 1512864-19-5 2,2'-(cyclohexylmethylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 85970-80-5 1-bromo-1-cyclohexylethylene 

Downstream Products

• 1202245-69-9 1‐cyclohexylethen-1-ylboronic acid 
• 894771-04-1 (R)-2-(1-cyclohexyl-ethyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 63167-00-0 (R)-N-benzyl-1-cyclohexylethylamine 

Relevant academic research and scientific papers

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

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.

Electrophilic Fluorination of Alkenes via Bora-Wagner–Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates

The electrophilic fluorination of geminal alkyl substituted vinyl-Bmida derivatives proceeds via bora-Wagner–Meerwein rearrangement. According to DFT modelling studies this rearrangement occurs with a low activation barrier via a bora-cyclopropane shaped TS. The Bmida group has a larger migration aptitude than the alkyl moiety in the Wagner–Meerwein rearrangement of the presented electrophilic fluorination reactions.

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.

Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene

Alkenyl boronic esters are important reagents in organic synthesis. Herein, we report that these valuable products can be accessed by the homologation of boronic esters with lithiated epoxysilanes. Aliphatic and electron-rich aromatic boronic esters provided vinylidene boronic esters in moderate to high yields, while electron-deficient aromatic and vinyl boronic esters were found to give the corresponding vinyl silane products. Through DFT calculations, this divergence in mechanistic pathway has been rationalized by considering the stabilization of negative charge in the C?Si and C?B bond breaking transition states. This vinylidene homologation was used in a short six-step stereoselective synthesis of the proposed structure of machillene, however, synthetic and reported data were found to be inconsistent.

Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift

Organoboron “ate” complexes undergo a net vinyl insertion reaction to give 1,1-disubstituted alkenyl boronic esters when treated with stoichiometric allyl acetate and a palladium catalyst. Reactions that employ vinyllithium afforded good to excellent yields after one hour, while reactions that employ vinylmagnesium chloride furnished modest to good yields after 18 hours.

Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction

A highly stereoselective boron-Wittig reaction between stable and readily accessible 1,1-bis(pinacolboronates) and aldehydes furnishes a variety of synthetically useful di- and trisubstituted vinyl boronate esters.

Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes

The highly selective copper-catalyzed hydroboration of allenes has been developed. Allylboranes and alkenylboranes were selectively prepared by the judicious choice of catalytic species (copper hydride and boryl copper). Furthermore, two types of alkenylboranes could be selectively synthesized by the choice of an appropriate ligand. Mechanistic studies confirmed that the protonation of a (Z)-σ-allyl copper species, which was isolated and structurally characterized by single-crystal X-ray diffraction, was a key step in these reactions. Besides allenes, this method is also applicable to the selective hydroboration of 1,3-diene derivatives to afford allylboranes and homoallylboranes. Copyright

Iridium-catalyzed enantioselective hydrogenation of alkenylboronic esters

Choose the right ligand: An iridium complex derived from a phosphino-imidazoline ligand is a highly efficient catalyst for the asymmetric hydrogenation of terminal vinyl boronic esters (see scheme). On the other hand, trisubstituted alkenyl-boronates can