116760-59-9

Upstream product

• 67-56-1 methanol 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 108-68-9 3,5-Dimethylphenol 
• 4962-29-2 4-methoxy-3,5-dimethylphenol 

Downstream Products

• 1027054-89-2 4,4-Dimethoxy-3,5-dimethyl-1-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-dienol 
• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 1431793-62-2 C₁₈H₂₂O₅ 
• 39785-37-0 4-amino-2,6-dimethylanisole 

Relevant academic research and scientific papers

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction

A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.

Efficient Coupling Reaction of Quinone Monoacetal with Phenols Leading to Phenol Biaryls

A simple and efficient synthesis of phenol biaryls by the cross-couplings of quinone monoacetals (QMAs) and phenols is reported. The Br?nsted acid catalytic system in 1,1,1,3,3,3-hexafluoro-2-propanol was found to be particularly efficient for this transformation. This reaction can be extended to the synthesis of various phenol biaryls, including sterically hindered biaryls, with yields ranging from 58 to 90 % under mild reaction conditions and in a highly regiospecific manner.

Practical Organocatalytic Synthesis of Functionalized Non-C2-Symmetrical Atropisomeric Biaryls

An organic acid catalyzed direct arylation of aromatic C(sp2)H bonds in phenols and naphthols for the preparation of 1,1′-linked functionalized biaryls was developed. The products are non-C2-symmetrical, atropoisomeric, and represent previously untapped chemical space. Overall this transformation is operationally simple, does not require an external oxidant, is readily scaled up (up to 98mmol), and the structurally diverse 2,2′-dihydroxy biaryl (i.e., BINOL-type), as well as 2-amino-2′-hydroxy products (i.e., NOBIN-type) are formed with complete regioselectivity. Density-functional calculations suggest that the quinone and imino-quinone monoacetal coupling partners are exclusively arylated at their α-position by an asynchronous [3,3]-sigmatropic rearrangement of a mixed acetal species which is formed insitu under the reaction conditions. An organic acid catalyzed direct arylation of aromatic C(sp2)H bonds in phenols and naphthols was developed. This transformation is operationally simple, does not require an external oxidant, is readily scaled up, and the structurally diverse biaryls are formed with complete regioselectivity. Density functional calculations suggest a mechanism involving a mixed-acetal formation/[3,3]-sigmatropic rearrangement sequence.

Lewis acid catalyzed [3+2] coupling of indoles with quinone monoacetals or quinone imine ketal

The one-pot synthesis of benzofuroindolines and tetrahydroindolo[2,3-b] indoles was accomplished through a mild and concise [3+2] coupling of indoles and quinone monoacetals or quinone imine ketal promoted by a Lewis acid. A wide variety of benzofuroindolines and tetrahydroindolo[2,3-b]indoles were prepared in moderate to good yields. Copyright

TRANSITION METAL FREE METHODS OF SYNTHESIS OF BIARYL COMPOUNDS

The present disclosure provides methods of preparing biaryl compounds which do not require transition metal catalysts. In yet another aspect, the present disclosure provides pharmaceutical compositions comprising compounds as described herein and pharmaceutically acceptable carriers.

BIARYL COMPOUNDS AS ANTIMICROBIAL AND CHEMOTHERAPEUTIC AGENTS

In one aspect, the present disclosure provides diaryl compounds of the formula presented herein. The application also provides compositions and methods of treatment thereof. In some embodiments, these compounds are used in the treatment of bacterial infec

Direct synthesis of anilines and nitrosobenzenes from phenols

A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

Br?nsted acid-controlled [3 + 2] coupling reaction of quinone monoacetals with alkene nucleophiles: A catalytic system of perfluorinated acids and hydrogen bond donor for the construction of benzofurans

We have developed an efficient Br?nsted acid-controlled strategy for the [3 + 2] coupling reaction of quinone monoacetals (QMAs) with nucleophilic alkenes, which is triggered by the particular use of a specific acid promoter, perfluorinated acid, and a solvent, fluoroalcohol. This new coupling reaction smoothly proceeded with high regiospecificity in regard with QMAs for introducing π-nucleophiles to only the carbon α to the carbonyl group, thereby providing diverse dihydrobenzofurans and derivatives with high yields, up to quantitative, under mild conditions in short reaction times. The choice of Br?nsted acid enabled us to avoid hydrolysis of the QMAs, which gives quinones, and the formation of discrete cationic species from the QMAs. Notably, further investigations in this study with regard to the acid have led to the findings that the originally stoichiometrically used acid could be reduced to a catalytic amount of 5 mol % loading or less and that the stoichiometry of the alkenes could be significantly improved down to only 1.2 equiv. The facts that only a minimal loading (5 mol %) of perfluoroterephthalic acid is required, readily available substrates can be used, and the regioselectivity can be controlled by the acid used make this coupling reaction very fascinating from a practical viewpoint.

Efficient synthesis of oxygenated terphenyls and other oligomers: Sequential arylation reactions through phenol oxidation-rearomatization

One by one: Starting from simple phenols, a diverse series of oxygenated terphenyl compounds can be prepared in a concise and practical manner using sequential arylation reactions involving phenol oxidation/rearomatization and quinone monoacetal intermediates (see scheme). Many of the terphenyl products can be used for preparing well-defined oligomers and, furthermore, contain valuable functional groups that can be transformed for further diversification. Copyright

π-Facial Diastereoselection in Diels-Alder Reactions of (R)-4-[(p-Tolylsulfinyl)methyl]quinols

Diels-Alder reactions of a range of (R)-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones with cyclopentadiene and 1,3-pentadiene proceed in a total π-facial diastereoselective manner from the C-4 OH side. Ab initio calculations at the RHF/6-31G