66217-55-8

Usage

Type of Compound

Cyclic boronic ester

Usage

Widely used as a reagent in organic chemistry

Physical State

Colorless liquid

Molecular Weight

186.09 g/mol

Boiling Point

124-128°C

Applications

a. Building block in the synthesis of pharmaceuticals, agrochemicals, and materials
b. Reagent in organic synthesis, particularly in the Suzuki coupling reaction for carbon-carbon bond formation
c. Production of polymers and coordination compounds

Upstream product

• 23985-40-2 tricyclopentylborane 
• 67-63-0 isopropyl alcohol 
• 142-29-0 cyclopentene 
• 73183-34-3 bis(pinacol)diborane 
• 137-43-9 Cyclopentyl bromide 
• 34557-54-5 methane 
• 287-92-3 Cyclopentane 
• 930-28-9 cyclopentyl chloride 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 1003-03-8 Cyclopentamine 
• 3558-06-3 cyclopentyl tosylate 
• 32999-14-7 2-cyclopentyl-benzo[1,3,2]dioxaborole 
• 946513-95-7 1,3-dioxoisoindolin-2-yl cyclopentanecarboxylate 

Downstream Products

• 1040745-70-7 cyclopentyltrifluoro-λ⁴-borane potassium salt 

Relevant academic research and scientific papers

Catalyst-controlled selectivity in the C-H borylation of methane and ethane

The C-H bonds of methane are generally more kinetically inert than those of other hydrocarbons, reaction solvents, and methane functionalization products.Thus, developing strategies to achieve selective functionalization of CH4 remains a major

Insight into the copper-catalyzed borylation of strained alkenes

The copper-catalyzed hydro-and carboboration of strained alkenes is presented. The reaction is highly diastereoselective and affords boronic ester derivatives many of which are difficult to synthesize by known methods. Competition experiments with differe

Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis

Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).

Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters

An electrochemically promoted decarboxylative borylation reaction is reported. The reaction proceeds under mild conditions in an undivided cell without use of transition metal- or photo-catalysts. The key feature of the reaction is the compatibility of di

Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters

Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.

Photochemical synthesis method of alkyl borate compound

The invention discloses a photochemical synthesis method of an alkyl borate compound. By taking alkane and duplex catechol borate as raw materials, coupling of carbon-boron bonds is realized under ultraviolet light illumination in the presence of an additive, and separating and purifying are carried out to obtain the alkyl borate compound. The photochemical synthesis method has the characteristics of high atom economy, greenness, high efficiency, avoidance of use of an oxidizing agent, simple process and the like, and is suitable for large-scale production.

Visible-light-driven graphene supported Cu/Pd alloy nanoparticle-catalyzed borylation of alkyl bromides and chlorides in air

A highly efficient photocatalytic protocol for borylation of alkyl bromides and chlorides with graphene supported Cu/Pd alloy nanoparticles as a heterogeneous catalyst is reported. This photocatalytic system operates with visible light in air, providing a wide range of primary and secondary alkyl halides with B2pin2 or B2neop2 in high yields at low temperatures, thereby demonstrating its broad utility and functional group tolerance. The high performance is attributed to a synergistic effect of localized surface plasmon resonance (LSPR) of Cu and charge transfer from Cu to Pd due to the alloy surface charge heterogeneity. Transfer of energetic electrons from Pd to electrophilic alkyl halides lead to the formation of the alkyl radicals, which quickly react with a nucleophilic adduct of a diboron compound with base adsorbed on the positively charged Cu sites to form the corresponding borylation product.

Light-Mediated Sulfur-Boron Exchange

Interaction of sulfides bearing a tetrafluoropyridinyl group with bis(catecholato)diboron followed by treatment with pinacol and triethylamine affording pinacol boronic esters is described. The reaction is promoted by an organic photocatalyst (3DPA2FBN) u

Method for directly preparing alkyl borate compound from alkyl halide

The invention relates to a method for directly preparing an alkyl borate compound from an alkyl halide, which comprises the following steps: in a protective atmosphere, mixing a titanium metal catalyst, an alkali compound, a borate compound and an alkyl halide or sulfonate compound, reacting at 35-100 DEG C for 8-24 hours, so that the alkyl halide or sulfonate compound is directly converted into the alkyl boronic acid pinacol ester compound. The method is simple to operate, low in cost, good in functional group tolerance and wide in substrate application range.

Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst

An unprecedented and general titanium-catalyzed boration of alkyl (pseudo)halides (alkyl-X, X=I, Br, Cl, OMs) with borane (HBpin, HBcat) is reported. The use of titanium catalyst can successfully suppress the undesired hydrodehalogenation products that prevail using other transition-metal catalysts. A series of synthetically useful alkyl boronate esters are readily obtained from various (primary, secondary, and tertiary) alkyl electrophiles, including unactivated alkyl chlorides, with tolerance of other reducing functional groups such as ester, alkene, and carbamate. Preliminary studies on the mechanism revealed a possible radical reaction pathway. Further extension of our strategy to aryl bromides is also demonstrated.