86694-55-5

Upstream product

• 534-22-5 2-methylfuran 
• 123-11-5 4-methoxy-benzaldehyde 
• 1236810-91-5 N-((4-methoxyphenyl)(2,4,6-trimethoxyphenyl)methyl)toluenesulfonamide 
• 14674-38-5 N-(4-methoxybenzylidene)-p-toluenesulfonamide 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 126810-30-8 C₁₈H₁₈OS₂ 
• 126810-27-3 2-[(4-Methoxy-phenyl)-(5-methyl-thiophen-2-yl)-methyl]-5-methyl-furan 

Relevant academic research and scientific papers

Sulfonated Tetraphenylethylene-Based Hypercrosslinked Polymer as a Heterogeneous Catalyst for the Synthesis of Symmetrical Triarylmethanes via a Dual C-C Bond-Cleaving Path

A sulfonic acid functionalized tetraphenylethylene-based hypercrosslinked polymer (THP-SO 3H) with a well-developed porous network and accessible sulfonic acid sites was synthesized and characterized by different analytical techniques. The cata

Anodically Triggered Aldehyde Cation Autocatalysis for Alkylation of Heteroarenes

Alkylation of heteroarenes by using aldehydes is a direct approach to increase molecular complexity, which however often involves the use of stochiometric oxidant, strong acid, and high temperature. This study concerns an energy-efficient electrochemical alkylation of heteroarenes by using aldehydes under mild conditions without mediators. Interestingly, the graphite anode can trigger aldehyde cationic species, which act as the effective autocatalysts to react with a range of heteroarenes to produce the corresponding products with excellent regioselectivity and in high yields. Compared to the traditional electro-synthesis approaches, this electro-triggered reaction provides an electricity-saving and eco-friendly route to high-value chemicals.

A two-phase system for the clean and high yield synthesis of furylmethane derivatives over -SO3H functionalized ionic liquids

A new and effective unique two-phase reaction system is investigated for the high yield production of tri(furyl)methane from furfural and furan. This strategy includes the use of an acidic aqueous phase (water + -SO3H functionalized IL) and furan phase, which significantly suppresses polymer formation, thereby increasing the yield of tri(furyl)methane. Furan serves as a reactant as well as an extraction solvent for the recovery of the condensation products. For comparison, different -SO3H functionalized ionic liquids are prepared and their performances evaluated for the condensation of furan and furfural. The ionic liquids with alkyl chain linkers are found to be more effective and acidic than those with imidazolium linked N-sulfonic acids. In addition, an increase in carbon chain length between imidazole/tri-ethylamine/pyridine and -SO3H, increases the catalytic activity of the respective ionic liquids. Among the several prepared ionic liquids, the strongly acidic imidazolium based butylsulfonic acid 6 shows the best activity with a maximum condensation product yield of 84%. This strategy offers a significantly high yield of the condensation products of furan and furfural compared to the traditional mineral acid route. The activity and stability of the -SO3H functionalized 6 is confirmed from seven successful recycles, in which there is no reduction in its activity. Finally, this new strategy is successfully extended for the condensation of furan derivatives (e.g. furan and 2-methylfuran) with several different aldehydes, ketones and alcohols.

CuBr2-catalyzed alkylation of furans with benzyl alcohols and benzaldehydes. Domino reactions including this alkylation as a key step

A CuBr2-catalyzed alkylation of furans with a broad scope of benzyl alcohols and benzaldehydes is reported. Reaction proceeds efficiently under mild reaction conditions requiring no inert atmosphere or other precautions. Moreover, it is shown that CuBr2 catalyzes domino reactions of furans with benzyl alcohols or benzaldehydes bearing a nucleophilic moiety in the ortho-position. These protocols offer a practical approach to densely substituted heterocyclic motifs from easily available furans.

An Unexpected C-C Bond Cleavage of Acetophenones: Synthesis of Bis(heteroaryl)arylmethanes and Triarylmethanes via SeO2/Lanthanide Chloride Catalyzed Friedel-Crafts Arylation

A novel synthesis of bisheteroarylaryl methanes and triarylmethanes is described by the selective C-C bond cleavage of acetophenones in the presence of SeO2/lanthanide chlorides. The present strategy provides an in situ generation of aldehydes from acetophenones followed by a double Friedel-Crafts reaction of electron-rich arenes. Natural product 1,1,1-tris(3-indolyl)methane is synthesized in a single step following the same protocol.

Green synthesis and anti-inflammatory studies of a series of 1,1-bis(heteroaryl)alkane derivatives

Molecular iodine has been used as an efficient catalyst for a double Friedel-Crafts reaction of various heteroarenes, i.e. 2-methylfuran, 2-ethylfuran, 2-methylthiophene, pyrrole, N-methylpyrrole and indole, using aldehydes as alkylating agents under "open-flask" conditions with toluene or water as the reaction media. In the presence of 10 mol% iodine in toluene at room temperature, both aliphatic and aromatic aldehydes reacted smoothly to give the corresponding bis(heteroaryl)alkanes in good to excellent yields. Interestingly, with water as the solvent, the bis(heteroaryl)alkane adducts were obtained in moderate to good yields. The use of mild reaction conditions, low catalyst loadings, and eco-friendly reagents in a single step synthesis are the advantages of the present procedure. In an effort to discover novel non-steroidal anti-inflammatory agents, the synthesized bis(heteroaryl)alkanes were evaluated for the anti-inflammatory activity in the lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage model. These compounds (50 μM) significantly inhibited NO production and did not exhibit significant cytotoxic effects on macrophage cells. Among them, bis[(5-methyl)2-furyl](4- nitrophenyl) methane exhibited the most potent inhibition of NO with IC 50 value of 42.4 ± 1.9, which is similar to that of the positive control, aminoguanidine (43.3 ± 2.5 μM). Thus, the bis[(5-methyl)2-furyl](4-nitrophenyl) methane could be considered a lead compound for the development of novel anti-inflammatory agents.

Cu(OTf)2 catalyzed synthesis of bis(5-methyl-2-furyl)methanes by condensation of 2-methylfuran with carbonyl compounds under solvent free conditions

A facile and efficient one-pot three-component synthesis of bis(5-methyl-2-furyl)methanes has been achieved via the reaction of 2-methylfuran with a series of aliphatic and aromatic aldehydes and aliphatic ketones in presence of copper(II) triflate under solvent free conditions. The bis(5-methyl-2-furyl)methanes were obtained in 34%-72% yields and the catalyst was recycled up to four successive cycles without much loss in catalytic activity. Copyright

Friedel-crafts arylation reactions of N -sulfonyl aldimines or sulfonamidesulfones with electron-rich arenes catalyzed by FeCl 3·6H2O: Synthesis of triarylmethanes and bis-heteroarylarylmethanes

(Figure presented) The FeCl3·6H2O-catalyzed Friedel-Crafts arylation reactions of N-sulfonyl aldimines or sulfonamidesulfones with electron-rich arenes and heteroarenes, which lead to the formation of triarylmethanes and bis-heteroar

NEW SYNTHESIS OF SUBSTITUTED DIFURYL OR DITHIENYL METHANES

New trisubstituted methanes derivatives are quantitatively and selectively obtained by condensation of 2-methylfuran or 2-methylthiophene with diverse aldehydes using macroporous ion-exchange resin as catalyst.Hydration rate of organic phase and sulfonic sites of catalyst determines a proper reaction progress.