87100-15-0

Usage

Uses

Cyclohexylboronic acid, pinacol ester

InChI:InChI=1/C12H23BO2/c1-11(2)12(3,4)15-13(14-11)10-8-6-5-7-9-10/h10H,5-9H2,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 32999-09-0 2-cyclohexylbenzo-[d][1,3,2]dioxaborole 
• 542-18-7 cyclohexyl chloride 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 110-83-8 cyclohexene 
• 110-82-7 cyclohexane 
• 73183-34-3 bis(pinacol)diborane 
• 931-50-0 cyclohexylmagnesium bromide 
• 1350934-26-7 5-cyclohexyl-5,6-dihydrobenzo[e]pyrazolo[1,5-c][1,3,2]diazaborinine 
• 766-77-8 Dimethylphenylsilane 
• 4441-56-9 cyclohexylboronic acid 
• 626-62-0 Cyclohexyl iodide 
• 108-93-0 cyclohexanol 
• 108-85-0 1-bromocyclohexane 

Downstream Products

• 87100-31-0 2-(chloro(cyclohexyl)methyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1136153-75-7 N-((2S)-2-cyclohexyl-2-hydroxy-2-phenylethyl)-2-methylpropane-2-sulfonamide 
• 1136153-66-6 N-((1S,2S)-2-cyclohexyl-2-hydroxy-1-phenylethyl)-2-methylpropane-2-sulfonamide 
• 1240816-22-1 (S)-2-[1-(4-chlorophenyl)-1-cyclohexylethylyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1240816-00-5 (S)-2-(1-cyclohexyl-1-phenylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1240816-34-5 (S)-2-[1-(4-fluorophenyl)-1-cyclohexylethylyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1313717-85-9 C₂₁H₃₃BO₂ 
• 1240816-64-1 (S)-2-[1-cyclohexyl-1-(2-methoxyphenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1240815-89-7 (S)-2-(1-cyclohexyl-1-phenylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

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.).

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

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

Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt**

An unprecedented and general hydroboration of alkenes with BX3 (X=Br, Cl) as the boration reagent in the presence of iPr2NEt is reported. The addition of iPr2NEt not only suppresses alkene polymerizat

Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation

Selective carbon-carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2-Csp3 and Csp2-Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C-C bond activation to afford two C-B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C-B bond formation and C-C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C-C bond activation. This journal is

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

Chromium-Catalyzed Borylative Coupling of Aliphatic Bromides with Pinacolborane by Hydrogen Evolution

The chromium-catalyzed borylative coupling between aliphatic bromides and pinacolborane (HBpin) is described. This reaction was promoted by low-cost and bench-stable CrCl3as a precatalyst combined with 4,4′-di-tert-butyl-2,2′-dipyridyl and aluminum, presenting a rare example of using HBpin as a borane reagent by coupling with alkyl bromides in forming borylated alkanes. Mechanistic studies indicate that aluminum plays important roles in the formation of reactive Cr species and aliphatic radicals, which lead to (alkyl)Cr by reaction with HBpin to give the products.

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.