102860-77-5

Upstream product

• 530-48-3 1,1-Diphenylethylene 
• 14284-89-0 manganese(III) acetylacetonate 
• 123-54-6 acetylacetone 
• 4110-55-8 3,5-diacetylheptane-2,6-dione 
• 98-86-2 acetophenone 
• 100-58-3 phenylmagnesium bromide 
• 599-67-7 1,1-diphenylethanol 
• 1694-29-7 3-chloropentane-2,4-dione 
• 28752-82-1 2-(allyloxy)benzaldehyde 

Downstream Products

• 13280-69-8 1-methyl-4-phenylnaphthalene 
• 55004-95-0 5,5-diphenyl-4-penten-2-one 

Relevant academic research and scientific papers

Silver-catalyzed radical reaction of 2H-indazoles with 1,3-dicarbonyl compounds to access 3-dicarbonyl indazoles

A convenient strategy for the direct synthesis of 3-substituted-2H-indazole derivatives was developed in the presence of AgNO3/Na2S2O8 under mild reaction conditions. The reaction affords a series of 1,3-dicarbonyl-2H-indazoles products with yields of up to 82%. The mechanism of the strategy suggests that the reaction proceeds through a radical pathway. Moreover, this strategy provides a new protocol for the synthesis of functionalized 2H-indazoles.

Advanced Synthesis of Dihydrofurans: Effect of Formic Acid on the Mn(III)-Based Oxidation

The Mn(III)-based oxidation of a tertiary alkylamine, such as nitrilotris(ethane-2,1-diyl) tris(3-oxobutanoate) (1) with 1,1-diphenylethene (2a), effectively proceeded in an acetic acid-formic acid mixed solvent to give nitrilotris(ethane-2,1-diyl) tris(2-methyl-5,5-diphenyl-4,5-dihydrofuran-3-carboxylate) (3). Other typical Mn(III)-based reactions of various β-diketo esters 4a-e, 2,4-pentanedione (6a), malonic acid (6b), and diethyl malonate (6c) with 1,1-diarylthenes 2a-d were also investigated in a similar acetic acid-formic acid mixed solvent and the reaction rate was accelerated and the product yield increased.

Can-mediated oxidative free radical reactions in an ionic liquid

Cerium(IV) ammonium nitrate-mediated oxidative radical reactions are carried out in the presence of ionic liquids, including 1-butyl-3-methylimidazolium tetrafluoroborate, for the first time. The presence of the ionic liquid not only increases the rate and yield of reactions in dichloromethane but also extends the range of 1,3-dicarbonyl precursors, which can be utilized in these carbon-carbon bond-forming reactions.

Facile access to highly-substituted dihydrofurans using resonated vinylpentanedione radicals generated by Mn(III)-based oxidation

Useful and easy access to highly-substituted dihydrofurans, which convert into various acetals, was established using the common Mn(III) oxidation. The key point is to use resonated vinylpentanedione radicals that cyclize to produce the desired acetoxydih

Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ-Unsaturated Ketones

A synthetic procedure, catalysed by Ir(ppy)3 under visible-light irradiation, for the chemodivergent synthesis of 2,3-dihydrofurans (3) or β,γ-unsaturated ketones (7) starting from α-halo ketones (1) and alkenes (2) has been developed. The mild reaction conditions and the redox-neutral nature of the process make it particularly sustainable avoiding the use of both sacrificial reactants and stoichiometric strong oxidants. Careful experimental investigations, supported by DFT calculations, allowed to disclose in details a possible mechanistic pathway and to direct the synthesis chemodivergently either toward 3 or 7, depending not only on the nature of the substrates, but also on the choice of the experimental conditions. (Figure presented.).

Silver-Catalyzed Radical Cascade Cyclization toward 1,5-/1,3-Dicarbonyl Heterocycles: An Atom-/Step-Economical Strategy Leading to Chromenopyridines and Isoxazole-/Pyrazole-Containing Chroman-4-Ones

A novel and convenient silver-catalyzed radical cascade cyclization toward a large variety of 1,5-/1,3-dicarbonyl heterocycles containing a chroman-4-one, indanone, or 2,3-dihydroquinolin-4(1H)-one moiety was developed, by reacting various 2-functionalized benzaldehydes, including 2-allyloxy benzaldehydes, 2-allyl benzaldehyde, and 2-N(Ts)CH2-CH CH2 substituted benzaldehyde, with 1,3-dicarbonyl compounds in the presence of AgNO3/K2S2O8 in one pot under mild reaction conditions. The newly obtained 1,5-/1,3-dicarbonyl-containing heterocycles were further used directly to synthesize more structurally diverse polyheterocycles, mainly including chromenopyridines as well as isoxazole- or pyrazole-containing chroman-4-ones.

Evidence of CuI/CuII Redox Process by X-ray Absorption and EPR Spectroscopy: Direct Synthesis of Dihydrofurans from β-Ketocarbonyl Derivatives and Olefins

The CuI/CuII and CuI/CuIII catalytic cycles have been subject to intense debate in the field of copper-catalyzed oxidative coupling reactions. A mechanistic study on the CuI/CuII redox proc

Maneanese(III)-Mediated Intermolecular Cyclization Reaction Alkenes and Active Methylene Compounds

The reaction of 1,1-diphenylethene 1,1-bis(4-chlorophenyl)ethene, 1,1-bis(4-methylphenyl)ethene, and 1,1-bis(4-methoxyphenyl)ethene with 3,5-diacetyl-2,6-hepatanedione in the presence of manganese(III) acetate in acetic acid at 80° yielded 4,6-dacetyl-8,8-diaryl-1,3-dimethyl-2,9-dioxabicyclo[4.3.0]non-3-enes (41-48%), 5-acetyl-2,2-diaryl-6-methyl-dihydrobenzo[b]furans (20-21%), 3-acetyl-5,5-diaryl-2-methyl-4,5-dihydrofurans (5-10%), and benzophenones (3-7%). Similarity, the reactions of 1,1-diarylethenes with dimethyl 2,4-diacetyl-1,5-pentanedioate or diethyl 2,4-diacetyl-1,5-pentanedioate gave the corresponding 4,6-bis(alkycarbonyl)-8,8-diaryl-1,3-dimethyl-2,9-dioxabicyclo[4.3.0]non-3-enes in moderate yields.

Formation of 1,2-Dioxanes by the Use of Tris(2,4-pentanedionato)manganese(III) or Manganese(III) Acetate

The reactions of 1,1-diphenylethene, 1,1-bis(4-chlorophenyl)ethene, 1,1-bis(4-methoxyphenyl)ethene, 1,1-bis(4-methylphenyl)ethene, 1,1-bis(4-fluorophenyl)ethene, styrene, 1-octene, cyclohexene, and cyclooctene with tris(2,4-pentanedionato)manganese(III) () in acetic acid at room temperature give 4-acetyl-3-methyl-1,2-dioxan-3-ol in 8-92percent yields, together with 3-acetyl-4-hydroxy-3-hexene-2,5-dione.The similar reactions of 1,1-diphenylethene with 2,4-pentanedione, 3-methyl-2,4-pentanedione, 3-ethyl-2,4-pentanedione, 1-phenyl-1,3-butanedione, acetoacetanilide, and 1,3-cyclohexanedione in the presence of manganese(III) acetate also give the corresponding cyclic peroxide in good to moderate yields.The mechanisms of manganese(III)-induced 1,2-dioxane ring formation and concomitant radical side reaction are discussed.

The Facile Synthesis of Dihydrofurans by the Oxidation of Olefins with Tris(2,4-pentanedionato)manganese(III)

Eleven olefins were oxidized with tris(2,4-pentanedionato)manganese(III) at the reflux temperature to give the corresponding 3-acetyl-2-methyl-4,5-dihydrofurans in good yields.The oxidation of 9-benzylidene-9,10-dihydroanthracene under the same reaction conditions did not produce the corresponding dihydrofuran, but 9--9,10-dihydroxyanthracene.When 1,1-diphenylethene was oxidized at room temperature, 3-acetyl-2-hydroperoxy-2-methyl-5,5-diphenyltetrahydrofuran was obtained in a high yield.The effects of the solvent and the additives on the yield of dihydrofuran, the comparable reactivities of other (2,4-pentanedionato)metal complexes, such as Co(III), Cr(III), Fe(III), and Cu(II), and the reaction mechanism are discussed.