2862-92-2

Upstream product

• 917-64-6 methyl magnesium iodide 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 2815-37-4 6-phenyl-1-oxaspiro[2.5]octane 
• 91909-96-5 5-Phenylcyclohexan-2-on-carbonsaeure-⁽¹⁾ 
• 75-16-1 methylmagnesium bromide 
• 87143-17-7 4-phenyl-1-methylenecyclohexane 
• 1603-60-7 1-methyl-4-phenylcyclohexane 

Downstream Products

• 64544-51-0 4-methyl-1,2,3,6-tetrahydro-1,1'-biphenyl 
• 87143-17-7 4-phenyl-1-methylenecyclohexane 
• 1380313-62-1 ((1s,4s)-4-bromo-4-methylcyclohexyl)benzene 
• 1380313-75-6 4,4,5,5-Tetramethyl-2-((1s,4s)-1-methyl-4-phenylcyclohexyl)-1,3,2-dioxaborolane 
• 1615227-13-8 (4-bromo-4-methylcyclohexyl)benzene 
• 1615227-20-7 2-(4-(4-methoxyphenyl)-2-methylbutan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes

Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.

Photoinduced Fragmentation Borylation of Cyclic Alcohols and Hemiacetals

A visible-light photoinduced fragmentation borylation of O-phthalimido cycloalkanols with bis(catecholato)diboron is described. Structurally diverse keto and formyloxy alkyl boronic esters are shown to be conveniently prepared by radical-mediated ring opening of cyclic alcohols and hemiacetals, respectively. The reactions proceed under mild conditions in the absence of additives or photocatalysts, display excellent functional group tolerance, and are shown to allow cleavage of 4-, 5-, 6-, and 7-membered ring substrates. The mechanism proceeds via sequential homolytic N-O and C-C bond cleavages, the latter of which involves β-scission of an alkoxy radical, generating a carbonyl and an alkyl radical that is trapped by the diboron reagent. Spectroscopic studies suggest direct photoexcitation of either the phthalimide or diboron substrates with blue light can initiate a radical chain mechanism.

Dehydroxylative Fluorination of Tertiary Alcohols

A large number of fluorination methods have been developed, but the construction of a tertiary C-F bond remains challenging. Herein, we describe an efficient dehydroxylative fluorination of tertiary alcohols with Selectfluor via the activation of a hydroxyl group by a Ph2PCH2CH2PPh2/ICH2CH2I system. Although the reagents appear to be not compatible (Selectfluor with the phosphine and I- generated in situ), the reactions occur rapidly to give the desired products in moderate to high yields. This work may present a new discovery in fluorination of alcohols since the reported methods are mainly limited to primary and secondary alcohols.

Direct Oxidation of Csp3?H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow

A fast, scalable, and safer Csp3?H oxidation of activated and un-activated aliphatic chains can be enabled by methyl(trifluoromethyl)dioxirane (TFDO). The continuous flow platform allows the in situ generation of TFDO gas and its rapid reactivity toward tertiary and benzylic Csp3?H bonds. The process exhibits a broad scope and good functional group compatibility (28 examples, 8–99 %). The scalability of this methodology is demonstrated on 2.5 g scale oxidation of adamantane.

Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor

Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.

SULFUR YLIDES IN REACTIONS WITH 4-SUBSTITUTED CYCLOHEXANONES: STEREOCHEMISTRY AND REACTIVITY

The stereochemistry of the epoxidation reactions of the title compounds (R= Me, Et, t-Bu, Ph, p-F-Ph, OMe, OH, CF3, OCOPh) with sulfur ylides (dimethylsulfonium methylide and dimethyloxosulfonium methylide) has been determined in three different solvents (DMSO, C6H6 and THF).Relative rates have been measured and the kinetic constants kcis and ktrans determined.

Oxidations of Alkylbenzenes with Dimethyldioxirane

Dioxiranes, Dimethyldioxirane, Alkylbenzenes, Oxidation The oxidation of various alkylbenzenes (1-17) with excess dimethyldioxirane (DMDO) in homogeneous acetone solutions has been studied.In general, the benzylic methylene and methine C-H bonds were oxidized to give the corresponding phenones and tertiary benzylic alcohols, respectively, in relatively low yields.Whereas a tert-butyl substituent at the reaction centre leads to very low conversion due to steric hindrance, the presence of additional phenyl groups appears to favour the oxidation in most,but not all cases.Di- and triphenylmethane (4 and 14) were found to be considerably less reactive than cis-decalin.By contrast, the intramolecular competetive oxidation of isobutylbenzene (19) and 1-methyl-4-phenylcyclohexanes (20) reveals that the benzylic C-H bonds are slightly more reactive than the tertiary ones at remote positions.