53535-83-4

Upstream product

• 38050-71-4 9-methoxy-9-BBN 
• 110-83-8 cyclohexene 
• 280-64-8 9-bora-bicyclo[3.3.1]nonane 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 39105-81-2 (dichloro)(cyclohexyl)borane 
• 5259-72-3 cyclo-octa-1,5-diene 
• 108-85-0 1-bromocyclohexane 
• 21205-91-4 9-borabicyclo[3.3.1]nonane dimer 
• 372-46-3 fluorocyclohexane 
• 280-64-8 9-borabicyclo[3.3.1]nonane 
• 446065-11-8 cyclohexyltrifluoro-λ⁴-borane potassium salt 
• 455-30-1 (cyclohexyl)difluoroborane 

Downstream Products

• 4354-72-7 2-cyclohexylmalononitrile 
• 29770-68-1 2-Chlor-2-cyclohexyl-acetonitril 
• 29770-75-0 2-Cyclohexyl-3-methyl-pentanonitril 
• 5653-09-8 2-cyclohexyl-1-phenylethan-1-one 
• 64705-65-3 (E)-1-Cyclohexyl-2-ethyl-1-octene 
• 1613-43-0 2-cyclohexylquinoline 
• 5292-21-7 Cyclohexylacetic acid 
• 13141-48-5 2-cyclohexyl-1H-indole 
• 108-93-0 cyclohexanol 
• 38050-71-4 9-methoxy-9-BBN 

Relevant academic research and scientific papers

Interactions of C?F Bonds with Hydridoboranes: Reduction, Borylation and Friedel–Crafts Alkylation

The stoichiometric reactions of the alkylfluorides 1-fluoroadamantane (Ad-F), fluorocyclohexane (Cy-F), 1-fluoropentane (Pent-F) and benzyl fluorides with secondary boranes pinacolborane (HBpin), catecholborane (HBcat), 9-borabicyclo(3.3.1)nonane (9-BBN)

Copper-catalyzed carboxylation of hydroborated disubstituted alkenes and terminal alkynes with cesium fluoride

A protocol for the hydrocarboxylation of disubstituted alkenes and terminal alkynes providing access to different secondary carboxylic acids and malonic acid derivatives has been developed. This methodology relies on an initial hydroboration using 9-BBN followed by carboxylation with carbon dioxide in the presence of a copper catalyst and the additive, cesium fluoride. Different cyclohexene, styrene, and stilbene derivatives could be utilized, and alkynes could be transformed into their corresponding dicarboxylic acids in good yields. Finally, six different terpenoids were carboxylated using the developed procedure. (Chemical Equation Presented).

Copper-Catalyzed Addition of Alkylboranes to Iminoacetates: Access to α-Alkyl Branched α-Amino Acids

A copper(I)-catalyzed addition of alkylborane reagents to α-iminoacetates has been developed to assemble both acyclic and cyclic α-branched α-amino carboxylic acid derivatives in good yields. A wide variety of unactivated alkenes are well tolerated in this transformation. (Figure presented.).

Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes

The scope of the copper-catalyzed coupling reactions between organoboron compounds and allylic phosphates is expanded significantly by employing triphenylphosphine as a ligand for copper, allowing the use of secondary alkylboron compounds. The reaction proceeds with complete γ-E-selectivity and preferential 1,3-syn stereoselectivity. The reaction of γ-silicon-substituted allylic phosphates affords enantioenriched α-stereogenic allylsilanes.

Phosphine-catalyzed anti-carboboration of alkynoates with alkyl-, alkenyl-, and arylboranes

We found that trialkylphosphine organocatalysts promoted unprecedented anti-carboboration of alkynoates with alkyl-, alkenyl-, or arylboranes to form β-boryl acrylates. The regioselectivity of the carboboration across the polar C-C triple bond exhibited inverse electronic demand, with the less electronegative B atom being delivered to the positively charged β carbon atom. The regioselectivity and the anti stereoselectivity were both complete and robust. In addition, the substrate scope was broad with excellent functional group compatibility.

Synthesis of alcohols from m-fluorophenylsulfones and dialkylboranes: Application to the C14-C35 building block of E7389

The reaction of m-fluorophenylsulfone anions with dialkylboranes, followed by alkaline hydroperoxide oxidation, yields alcohols in high yields. Optimization of the process, scope and limitation, and application to the synthesis of one of the C14-C35 building blocks of E7389, a right half analogue of halichondrin B, are reported.

Conversion of alkyltrifluoroborates into alkyldichloroboranes with tetrachlorosilane in coordinating solvents

Organotrifluoroborate salts are converted rapidly by tetrachlorosilane in nucleophilic solvents such as THF or acetonitrile into organodichloroboranes coordinated with the solvent (see scheme). This reaction completes a sequence from alkylboronic esters via the trifluoroborate salts to reactive alkyldichloroboranes under mild conditions.

Alkylation of nitroaromatics with trialkyborane

When p-dinitrobenzene is reacted with Et3B in t-BuOH or THF in the presence oft-BuOK, it yields p-nitroethylbenzene. In this report we examine the scope of this transformation by monitoring the effect of various parameters on the reaction. It has been found that the reaction is extremely sensitive to temperature and rather insensitive to the base-solvent combination used. It is also insensitive to the steric hindrance of the base: good yields were obtained using sodium 2,6-diisopropylphenoxide or when using NaH. Alkylation was obtained With a large variety of alkylboranes ranging from linear to polycyclic. Yields drop significantly if one of the nitro groups is replaced by another electron-withdrawing group. In all cases studied (CHO, PHCO, SO2Ph, and CN), it is the latter group which was preferentially displaced by the alkyl group. According to the suggested mechanism, the radical anion of the substrate combines with the alkyl radical released from the boranyl radical to form a Meisenheimer complex. The reaction takes place at the ring carbon bearing the highest spin density in accordance with ab initio calculations at the B3LYP/ 6-31+G level.

The enantioselective synthesis of α-amino acid derivatives via organoboranes

Optically active (S)-α-amino acids are prepared in 54-95% ee (12 cases) by reaction of the Schiff base acetate of glycine tert-butyl ester with B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine, and base. The enantiomeric (R)-α-amino acids are available in 59-92% ee (3 cases) by using cinchonine as the chiral control element. Copyright

Solid-phase synthesis of unnatural α-amino acid derivatives using a resin-bound glycine cation equivalent

Unnatural amino acids were synthesized on solid-phase by reaction of a resin-bound Schiff base with organoboranes. This novel use of a resin-bound glycine cation equivalent allows for the preparation of a variety of amino acid structural types not readily available by the complementary anionic equivalent.