17221-37-3

Upstream product

• 110-00-9 furan 
• 13014-92-1 acetic acid-(4-chloro-N-nitroso-anilide) 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 106-47-8 4-chloro-aniline 
• 196953-02-3 1-(4-chlorophenyl)buta-2,3-dien-1-one 
• 104-88-1 4-chlorobenzaldehyde 
• 106-39-8 bromochlorobenzene 
• 201230-82-2 carbon monoxide 
• 1679-18-1 4-Chlorophenylboronic acid 
• 107-19-7 propargyl alcohol 
• 584-12-3 2-bromofuran 
• 1445726-49-7 caesium furan-2-carboxylate 
• 20842-02-8 potassium furan-2-carboxylate 
• 2786-02-9 2-lithiofuran 

Downstream Products

• 149578-43-8 2-(4-chloro-phenyl)-furan-3,4-dicarboxylic acid diethyl ester 
• 62645-46-9 Bis-<5-(4-Chlorphenyl)-2-furyl>-methan 
• 87689-38-1 2-(p-Chlorophenyl)-5-dimethylaminomethylfuran hydrochloride 
• 56297-29-1 2-(4-chlorophenyl)-5-(4-nitrophenyl)furan 
• 1204-91-7 1-(4-nitrophenyl)-1H-1,2,3-triazole 
• 100-01-6 4-nitro-aniline 
• 69836-61-9 dimethyl 1-(4-chlorophenyl)-7-oxabicyclo[2.2.1] hepta-2,5-diene-2,3-dicarboxylate 
• 84185-74-0 4-(4-Chloro-phenyl)-7-hydroxy-isobenzofuran-1,3-dione 
• 84185-80-8 (E)-2-[5-(4-Chloro-phenyl)-furan-2-yl]-but-2-enedioic acid 
• 73226-76-3 2-Bromo-5-(4-chloro-phenyl)-furan 
• 73226-93-4 3,5-Dibromo-2-(4-chloro-phenyl)-furan 
• 56297-33-7 1-[5-(4-chloro-phenyl)-furan-2-yl]-propan-1-one 
• 41019-40-3 methyl 5-(4-chlorophenyl)furan-2-carboxylate 

Relevant academic research and scientific papers

Blue light mediated C-H arylation of heteroarenes using TiO2 as an immobilized photocatalyst in a continuous-flow microreactor

Titanium dioxide was applied as an immobilized photocatalyst in a microstructured falling film reactor for the continuous-flow C-H arylation of heteroarenes with aryldiazonium salts as the starting material. Detailed investigations of the catalyst and a successful long-term run proved its excellent usability for this process. Very good yields up to 99% were achieved with broad substrate scope and were compared with batch synthesis. The transfer to the continuous-flow mode revealed an impressive boost in reactor performance solely resulting from the improved irradiation and contact of the catalyst, substrate and light.

Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions

Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

Carbazole based Electron Donor Acceptor (EDA) catalysis for the synthesis of biaryl and aryl-heteroaryl compounds

A highly regioselective, carbazole based Electron Donor Acceptor (EDA) catalyzed synthesis of biaryl and aryl-heteroaryl compounds is described. Various indole and carbazole derivatives were screened for the Homolytic Aromatic Substitution (HAS) reaction. Tetrahydrocarbazole (THC) was very efficient for the HAS transformation and proceeded via a complex formation between diazonium salt and electron rich tetrahydrocarbazole. The UV-Vis spectroscopy technique has been used to confirm the complex formation. The in situ generated EDA complex even in a catalytic amount is found to be efficient for the Single Electron Transfer (SET) process without any photoactivation. Biaryl compounds, 2-phenylfuran, 2-phenylthiophene, and 2-phenylpyrrole and bioactive compounds such as dantrolene and canagliflozin have been synthesized in moderate to excellent yields.

Organic/Inorganic Heterogeneous Silica-Based Photoredox Catalyst for Aza-Henry Reactions

The transformation of light into chemical energy is a leitmotiv in the development of sustainable and environmentally concerned chemical processes. Chemists invented original concepts to address this purpose, like photoredox catalysis, which became a wond

Transition-Metal-Free Synthesis of Heterobiaryls through 1,2-Migration of Boronate Complex

The synthesis of a diverse range of heterobiaryls has been achieved by a transition-metal-free sp2–sp2 cross-coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl–heteroaryl boronate complex, which triggered 1,2-migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good yield. A comprehensive 11B NMR study has been conducted to support the mechanism. The cross coupling between two nucleophilic cross coupling partners without transition metals reveals a reliable manifold to procure heterobiaryls in good yields. Various heterocycles like furan, thiophene, benzofuran, benzothiophene, and indole are well tolerated. Finally, we have successfully demonstrated the gram scale synthesis of the intermediates for an anticancer drug and OLED material using our methodology.

Redox reactions of small organic molecules using ball milling and piezoelectric materials

Over the past decade, photoredox catalysis has harnessed light energy to accelerate bond-forming reactions. We postulated that a complementary method for the redox-activation of small organic molecules in response to applied mechanical energy could be dev

Phenalenyl Based Aluminum Compound for Catalytic C-H Arylation of Arene and Heteroarenes at Room Temperature

Main group metal based catalysis has been considered to be a cost-effective alternative way to the transition metal based catalysis, due to the high abundance of main group metals in the Earth's crust. Among the main group metals, aluminum is the most abundant (7-8%) in the Earth's crust, making the development of aluminum based catalysts very attractive. So far, aluminum based compounds have been popularly used as Lewis acids in a variety of organic reactions, but chemical transformation demanding a redox based process has never utilized an Al(III) complex as a catalyst. Herein, we tuned the redox noninnocence behavior of a phenalenyl ligand by coupling with Al(III) ion, which subsequently can store the electron upon reduction with K to carry out direct C-H arylation of heteroarenes/mesitylene at ambient temperature. A mechanistic investigation revealed that a three-electron reduced phenalenyl based triradical aluminum(III) complex plays the key role in such catalysis. The electronic structure of the catalytically active triradical species has been probed using EPR spectroscopy, magnetic susceptibility measurements, and electronic structure calculations using a DFT method.

Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight

Naturally occurring perylenequinonoid pigments (PQPs) have attracted considerable attention owing to their excellent properties of photosensitization. They have been widely investigated as an aspect of photophysics and photobiology. However, their applications in photocatalysis are yet to be explored. We report here that sunlight along with 1 mol% cercosporin, which is one of the perylenequinonoid pigments, catalyzes the direct C-H bond arylation of (het)arenes by a photoredox process with good regioselectivity and broad functional group compatibility. Furthermore, a gram-scale reaction with great conversions of substrates was achieved even by a cercosporin-containing supernatant without organic solvent extraction and purification after liquid fermentation. Thus we set up a bridge between microbial fermentation and organic photocatalysis for chemical reactions in a sustainable, environmentally friendly manner.

1-Aryltriazenes in the Suzuki, Heck, and Sonogashira Reactions in Imidazolium-ILs, with [BMIM(SO3H)][OTf] or Sc(OTf)3 as Promoter, and Pd(OAc)2 or NiCl2·glyme as Catalyst

1-Aryltriazenes, the protected and more stable form of aryl-diazonium species, can be conveniently unmasked with Br?nsted acidic-IL or Sc(OTf)3 and coupled with a host of aryl/heteroaryl boronic acids, styrenes, and aryl/alkyl acetylenes in the Suzuki, Heck and Sonogashira reactions in one-pot and in respectable isolated yields, by using palladium or nickel catalyst in readily available imidazolium ILs as solvent, under mild conditions. The scope of these reactions are explored, and the potential for recovery/reuse of the IL solvent is also addressed.

Cycloisomerization of Conjugated Allenones into Furans under Mild Conditions Catalyzed by Ligandless Au Nanoparticles

Au nanoparticles supported on TiO2 (1 mol %) catalyze the quantitative cycloisomerization of conjugated allenones into furans under very mild conditions. The reaction rate is accelerated by adding acetic acid (1 equiv), but the acid does not participate in the protodeauration step as in the corresponding Au(III)-catalyzed transformation. The process is purely heterogeneous, allowing thus the recycling and reuse of the catalyst effectively in several runs.