4481-56-5

Upstream product

• 2689-59-0 (furan-2-yl)(phenyl)methanone 
• 119-61-9 benzophenone 
• 98754-48-4 2-furylmagnesium bromide 
• 110-00-9 furan 
• 54829-48-0 2-iodofuran 
• 464-72-2 tetraphenylethane-1,2-diol 
• 22037-28-1 3-bromofurane 
• 79654-37-8 diphenyl(2-thienyl)methanol 
• 76-84-6 triphenylmethyl alcohol 
• 614-99-3 Ethyl 2-furoate 

Downstream Products

• 119-61-9 benzophenone 
• 18812-36-7 5-diphenylmethylene-2(5H)-furanone 
• 5432-54-2 (2-methylphenyl)diphenylmethanol 
• 79654-37-8 diphenyl(2-thienyl)methanol 
• 847-83-6 p-methoxytrityl alcohol 
• 64655-62-5 (2-methoxyphenyl)(diphenyl)methanol 
• 21856-96-2 Diphenyl<4-(trifluormethyl)phenyl>methanol 
• 6326-62-1 (biphenyl-2-yl)(diphenyl)methanol 
• 73475-34-0 [2-(trifluoromethyl)phenyl](diphenyl)methanol 
• 569674-01-7 (2,6-dimethylphenyl)(diphenyl)methanol 
• 132606-36-1 4-oxo-5,5-diphenyl-valeric acid 

Relevant academic research and scientific papers

Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2

Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.

Visible-light-mediated achmatowicz rearrangement

Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelfstable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4 as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.

Sodium-Ketyl Radical Anions by Reverse Pinacol Reaction and Their Coupling with Iodoarenes

Transition-metal-free C-C bond formation between aryl iodides and pinacols is presented. Pinacols are readily transformed by deprotonation with NaH to their Na-pinacolates. C-C-bond homolysis at room temperature generates in situ the corresponding Na-ketyl radical anions which react with various aryl iodides in a homolytic aromatic substitution reaction to form tertiary Na-alcoholates. Protonation eventually provides tertiary alcohols in an unprecedented route.

Generation and reactions of heteroaromatic lithium compounds by using in-line mixer in a continuous flow microreactor system at mild conditions

A lithium-halogen exchange reaction procedure was applied to introduce electrophilic substituents to the heteroaromatics, which exhibited potential in the syntheses of pharmaceutical intermediates. In this contribution, generation and reactions of heteroa

Deprotonation of furans using lithium magnesates

Furan was deprotonated on treatment with 1/3 equiv of Bu3MgLi in THF at rt. The lithium arylmagnesate formed was either trapped with electrophiles or involved in a palladium-catalyzed cross-coupling reaction with 2-bromopyridine. The highly coordinated magnesate Bu4MgLi2 (1/3 equiv) proved to be a better deprotonating agent than Bu3MgLi; the monitoring of the reaction using NMR spectroscopy showed that the deprotonation of furan at rt required 2 h whereas the subsequent electrophilic trapping was instantaneous. The method was extended to benzofuran, allowing its functionalization at C2 in high yields. The deprotonation of 2-methylfuran and lithium furfurylalkoxide at C5 turned out to be difficult, requiring either long reaction times or higher temperatures.

Palladium-catalyzed arylation of α,α-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls

The palladium-catalyzed arylation of α,α-disubstituted arylmethanols with aryl halides proceeds not only via C-H bond cleavage at the ortho-position, but also via cleavage of the sp2-sp3 C-C bond with the liberation of ketones (β-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C-C or C-H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. Thus, various biaryls having ortho-substituents can be produced efficiently by treatment of the corresponding aryl(diphenyl or dimethyl)methanols with aryl bromides and chlorides.