28093-86-9

Upstream product

• 67-56-1 methanol 
• 92-69-3 4-Phenylphenol 
• 4075-79-0 4-phenylacetanilide 
• 92-67-1 4-phenylalanine 
• 146474-20-6 N-Benzoyl-4-methoxy-4-phenyl-p-benzoquinol imine 
• 146474-21-7 4-Methoxy-4-phenyl-2,5-cyclohexadienone N-acetylimine 
• 103594-20-3 8-Methoxy-8-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-diene 
• 103594-13-4 (1,4,4-Trimethoxy-cyclohexa-2,5-dienyl)-benzene 

Downstream Products

• 122698-77-5 5-(1,3-dithian-2-yl)-4-methoxy-4-phenylcyclohex-2-en-1-one 
• 1312922-16-9 3-(4-methoxybiphenyl-2-yl)-1H-indole 
• 92-04-6 2-chloro-4-phenylphenol 
• 1431660-76-2 3,5-diphenyl-1H-indole 
• 122698-75-3 4,5-diphenyl-4-methoxy-2-cyclohexenone 
• 92-69-3 4-Phenylphenol 
• 122698-78-6 5-(2-(trimethylsilyl)ethynyl)-4-phenyl-4-methoxycyclohex-2-en-1-one 
• 122698-76-4 4-methoxy-4-phenyl-5-(2-propenyl)-2-cyclohexenone 

Relevant academic research and scientific papers

Copper-Catalyzed Chemo- and Diastereoselective 1,3-Dipolar Cycloaddition of Carbonyl Ylide and Aldehyde-Tethered-Cyclohexadienone to Access Polycyclic Systems

A copper-catalyzed tandem intermolecular ylide formation/intramolecular cycloaddition of diazo compounds and aldehyde-tethered-cyclohexadienones was reported, chemo- and diastereoselectively providing oxapolycyclic frameworks in moderate to excellent yields under mild conditions. This reaction creates two C?C bonds and one C?O bond with five stereocentres including two all-carbon quaternary centres. Moreover, the late-stage diversification of products can be realized via chemoselective substitutions. (Figure presented.).

Site-selective 1,3-double functionalization of arenes using: Para -quinol, C-N, and C-C/C-P three-component coupling

A catalytic and site-selective approach has been demonstrated for dual functionalization of arenes via cross-coupling reactions of p-quinols with amines and isocyanides/phosphites. The strategy enables the production of a series of 3-amino-benzamides and

Zinc-catalyzed regioselective C-P coupling of p-quinol ethers with secondary phosphine oxides to afford 2-phosphinylphenols

The zinc triflate-catalyzed highly regioselective C-P cross coupling reaction of p-quinol ethers with secondary phosphine oxides is reported. The reaction provides a facile alternative method for the synthesis of 2-phosphinylphenols in good to high yields. Mechanistically, zinc triflate may serve as an oxophilic σ-Lewis acid to activate the C-O bond in p-quinol ether first. Then the regioselective attack of the phosphorus nucleophile at the α-carbon position takes place to form the C-P bond and give the product. In addition, α-alkynyl substituted p-quinol ethers also react with secondary phosphine oxides in the same reaction mode to give 6-alkynyl 2-phosphinylphenols in the presence of the zinc catalyst.

Experimental evidence for the formation of cationic intermediates during iodine(iii)-mediated oxidative dearomatization of phenols

Iodine(iii)-based oxidants are commonly used reagents for the oxidative dearomatization of phenols. Having a better understanding of the mechanism through which these reactions proceed is important for designing new iodine(iii)-based reagents, catalysts, and reactions. We have performed a Hammett analysis of the oxidative dearomatization of substituted 4-phenylphenols. This study confirms that iodine(iii)-mediated oxidative dearomatizations likely proceed through cationic phenoxenium ions and not the direct addition of a nucleophile to an iodine-bound phenol intermediate.

Iodobenzene and m-chloroperbenzoic acid mediated oxidative dearomatization of phenols

Oxidative dearomatization of 2- and 4-substituted phenols to their corresponding benzoquinone monoketals by catalytic amount of iodobenzene, and m-CPBA as a co-oxidant has been achieved via in situ generation of PhIO2, a hypervalent iodine(V) s

Site-Selective Iron(III) Chloride-Catalyzed Arylation of 4-Aryl-4-methoxy-2,5-cyclohexadienones for the Synthesis of Polyarylated Phenols

The iron(III) chloride-catalyzed Friedel–Crafts arylation of 4-aryl-4-methoxy-2,5-cyclohexadienones, which were easily prepared by the phenyliodine(III) diacetate (PIDA)-mediated oxidation of 4-arylphenols in methanol, proceeded site-selectively to form meta-terphenyl (2,4-diarylphenol) derivatives in good yields. The subsequent PIDA-mediated oxidation and iron(III) chloride-catalyzed Friedel–Crafts arylation of the resulting products gave the corresponding 2,4,6-triarylphenol derivatives. The present method provides useful highly substituted polyarylated compounds. (Figure presented.).

Meta-selective substitution of phenols with indoles via one-pot oxidative dearomatization-Michael addition-aromatization

An oxidative coupling strategy involving hypervalent organoiodine-induced oxidative dearomatization of 4-substituted phenols, Br?nsted acid catalyzed Michael addition with indoles, and aromatization has been developed. The one-pot reaction provides an eff

Oxidation with hypervalent iodine reagents. Part II: Novel cyclohexadienones as precursors for the synthesis of anthraquinones

The oxidation of substituted phenols with phenyliodonium diacetate in methanol was found to afford 2,4-cyclohexadienones, 2,5-cyclohexadienones or mixtures of isomers, depending on the substrate being oxidized. Annulation of these cyclohexadienones with the anion of 3-cyanophthalide afforded anthraquinones in high yields.

The Electrochemical Preparation and Kinetic and Product Studies of Acylated Quinol and Quinol Ether Imines. In Search of the Hydrolysis Products of the "Ultimate" Carcinogen of N-Acetyl-2-aminofluorene

The N-acetyl and benzoyl derivatives of 4-methoxy-4-phenyl-2,5-cyclohexadienone imine and the N-benzoyl derivative of 4-hydroxy-4-phenyl-2,5-cyclohexadienone imine (1a-c) have been prepared via anodic oxidation of the corresponding amide of 4-aminobiphenyl in either methanol or water/ acetonitrile, respectively.The products and the kinetics of the acidic and basic hydrolyses of these compounds were studied and the results compared with other N-acylquinol imine derivatives, including N-acetyl-4-hydroxy-4-phenyl-2,5-cyclohexadienone imine (1d), generated by solvolytic routes.The chemistry of these compounds was dependent upon the pH and the substituents on the quinol imine derivative.The major reaction pathways were hydrolysis of the imine linkage to afford the respective dienone and phenyl migration to afford the amides of 2-hydroxy- or 2-methoxy-5-aminobiphenyl.The reactivity of the quinol imine derivatives follows the order: 4-hydroxyl more reactive than 4-methoxyl compounds and N-acetyl more reactive than N-benzoyl derivatives.The higher reactivity for the former compounds is attributed to the greater electron-donating ability of the 4-hydroxyl versus the 4-methoxyl group.The higher reactivity of the N-acetyl relative to the N-benzoyl derivatives is attributed to the ca. 30-fold increase in basicity of the N-acetyl functionality.The additive effect of the 4-hydroxyl and N-acetyl functionality on the basic quinol imine moiety makes compounds having both of the groups difficult to isolate in aqueous media.This serves as a limitation for the preparation of the quinol imine derivative of N-acetyl-2-aminofluorene via the anodic oxidation methods reported herein.

Oxidations Of Substituted Phenols With Hypervalent Iodine : Applications To The Phthalide Annulation Route To Anthraquinones

Substituted phenols are oxidized by phenyliodonium diacetate in methanol to yield either cyclohexa-2,4-dienones or the isomeric 2,5-dienones depending upon the structure of the phenol.Annulation of these oxidation products with the anion of 3-cyanophthali