879224-90-5

Upstream product

• 32999-09-0 2-cyclohexylbenzo-[d][1,3,2]dioxaborole 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 6947-57-5 cyclohexyl phenyl sulfone 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 108-93-0 cyclohexanol 
• 7570-92-5 cyclohexyl phenyl sulphide 
• 542-18-7 cyclohexyl chloride 
• 953-91-3 cyclohexyl tosylate 
• 110-83-8 cyclohexene 
• 108-85-0 1-bromocyclohexane 

Downstream Products

• 1136153-75-7 N-((2S)-2-cyclohexyl-2-hydroxy-2-phenylethyl)-2-methylpropane-2-sulfonamide 
• 945-49-3 (S)-cyclohexylphenylmethanol 
• 945-49-3 (R)-cyclohexylphenylmethanol 
• 1272031-58-9 (S)-2-[1-cyclohexyl-1-(2-fluorophenyl)ethyl]-5,5-dimethyl-1,3,2-dioxaborinane 
• 1272031-50-1 (R)-N-benzyl-[1-cyclohexyl-1-(2-fluorophenyl)ethyl]amine 
• 1240816-66-3 (S)-2-[1-cyclohexyl-1-(2-methoxyphenyl)ethyl]-5,5-dimethyl-1,3,2-dioxaborinane 
• 1240816-50-5 (S)-2-[1-(2-methylphenyl)-1-cyclohexylethyl]-5,5-dimethyl-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

Copper-catalyzed borylation of primary and secondary alkyl halides with bis(neopentyl glycolate) diboron at room temperature

Borylation reactions are heavily dependent on diboron agents, whose structures prescribe the reaction conditions. It necessitates extended investigation of borylation reactions using other diboron agents as a boron source than B2pin2

Base-Mediated Radical Borylation of Alkyl Sulfones

A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B2neop2), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.

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.

Iron-Based Catalyst for Borylation of Unactivated Alkyl Halides without Using Highly Basic Organometallic Reagents

The mild borylation of alkyl bromides and chlorides with bis(neopentylglycolato)diborane (B2neop2) mediated by iron-bis amide is described. The reaction proceeds with a broad substrate scope and good functional group compatibility. Moreover, sufficient ca

Cobalt(I)-Catalyzed Borylation of Unactivated Alkyl Bromides and Chlorides

A cobalt-complex-catalyzed borylation of a wide range of alkyl halides with a diboron reagent (B2pin2 or B2neop2) has been developed under mild reaction conditions, demonstrating the first cobalt-mediated cross-coupling with alkyl electrophiles. This protocol allows alkyl boronic esters to be accessed from alkyl halides, including alkyl chlorides, which were used rarely as coupling partners. Mechanistic studies reveal the possible involvement of an alkyl radical intermediate in this cobalt-mediated catalytic cycle.

Free Radical Pathway Cleavage of C—O Bonds for the Synthesis of Alkylboron Compounds

We report a silver-catalyzed borylation of alkyl tosylates, which provides a new method for the synthesis of alkylboron compounds with good functional group compatibility and excellent chemoselectivity. The present work added highly polarized alkyl tosylate C—O bonds to the fairly limited number of C—O bonds able to participate in free radical cleavage pathways. The mechanistic studies suggested that in situ-generated silver(0) catalytic species were the active catalytic species and played a key role in the radical pathway cleavage of C—O bonds.

Zinc-catalyzed borylation of primary, secondary and tertiary alkyl halides with alkoxy diboron reagents at room temperature

A new catalytic system based on a ZnII NHC precursor has been developed for the cross-coupling reaction of alkyl halides with diboron reagents, which represents a novel use of a Group XII catalyst for C=X borylation. This approach gives borylations of unactivated primary, secondary, and tertiary alkyl halides at room temperature to furnish alkyl boronates, with good functional-group compatibility, under mild conditions. Preliminary mechanistic investigations demonstrated that this borylation reaction seems to involve one-electron processes. Coupling a la carte: A catalytic system based on a ZnII N-heterocyclic carbene precursor has been developed for the cross-coupling reaction of alkyl halides with diboron reagents (see scheme). This is a novel use of a Group 12 catalyst for C=X borylation. IMes=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene. Copyright

Reagent-controlled asymmetric homologation of boronic esters by enantioenriched main-group chiral carbenoids

Putative enantioenriched carbenoid species, (R)-1-chloro-2- phenylethylmagnesium chloride (9) and (S)-1-chloro-2-phenylethyllithium (26), generated in situ by sulfoxide ligand exchange from (-)-(Rs,R)-1- chloro-2-phenylethyl p-tolyl sulfoxide (8), effected the stereocontrolled homologation of boronic esters. sec-Alcohols derived from the product boronates by oxidation with basic hydrogen peroxide exhibited % ee closely approaching that of sulfoxide 8 in examples employing Li-carbenoid 26.