5840-40-4

Upstream product

• 101-81-5 Diphenylmethane 
• 612-25-9 2-Nitrobenzyl alcohol 
• 552-89-6 2-nitro-benzaldehyde 
• 28059-64-5 2-benzylaniline 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 108-86-1 bromobenzene 
• 1316859-98-9 potassium 2-(2-nitrophenyl)acetate 
• 98-80-6 phenylboronic acid 
• 1493-27-2 ortho-nitrofluorobenzene 
• 108-88-3 toluene 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 108-90-7 chlorobenzene 
• 5570-19-4 2-nitrophenylboronic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 5176-14-7 3-phenyl-2,1-benzoxazole 
• 65-85-0 benzoic acid 
• 578-95-0 10H-acridin-9-one 
• 260-94-6 acridine 
• 69751-74-2 (2-amino-3,5-dibromophenyl)phenylmethanone 
• 147-82-0 2,4,6-tribromoaniline 
• 1721-92-2 2-methyl-4-phenylquinoline 
• 463954-80-5 2-(4-phenyl-1H-[2]chinolyLiDene)-indane-1,3-dione 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 4888-33-9 4-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 1316859-94-5 ethyl 3-(2-nitrophenyl)-3-phenylpropanoate 
• 1316859-92-3 3-(2-nitrophenyl)-1,3-diphenylpropan-1-one 
• 1039-51-6 2,4-diphenylquinoline 
• 1415487-49-8 C₂₂H₂₃NO₂ 

Relevant academic research and scientific papers

Superior Catalytic Performance of Hierarchically Micro-Meso-Macroporous CuAlPO-5 for the Oxidation of Aromatic Amines under Mild Conditions

Aromatic nitro compounds are versatile building blocks for organic synthesis because of easy transformation of the nitro group into other diverse functional groups. Herein, hierarchical mesoporous–macroporous CuAlPO-5 was prepared and found to exhibit excellent catalytic activity and stability for the oxidation of aromatic amines to nitroarenes. For the oxidation of bulky aromatic amine molecules (e.g., 1-naphthalenamine), hierarchical CuAlPO-5 exhibited higher selectivity to the product than homogeneous Cu catalysts and higher catalytic activity than traditional microporous CuAlPO-5; the former was attributed to shape selectivity to the product and the latter was attributed to improved diffusion of bulky molecules inside the meso- and macropores. After CuAlPO-5 was used five times in the oxidation of 4-bromoaniline, >98.6 % conversion and 98.1 % selectivity to the product were obtained. This shows the potential and attractiveness of this method for the preparation of nitroarenes by the selective oxidation of organic amines.

Synthesis of Dihydroanthracenes via Palladium-Catalyzed Tandem Mizoroki-Heck/Reductive Heck Reactions Using Cyclic Diaryliodoniums and Alkenes

An efficient Pd-catalyzed domino Mizoroki-Heck and reductive Heck reaction of terminal alkenes with six-membered cyclic diaryliodoniums is reported for the facile access to a diverse set of novel dihydroanthracenes. The scope of alkenes is general, leading to concise generation of 30 dihydroanthracenes which are not easily accessed by conventional methods. Furthermore, one of the newly synthesized dihydroanthracene displayed excellent antiproliferative activity against PANC-1 cancer cells (IC 50= 11.74 μM).

Copper-Catalyzed Selective Arylation of Nitriles with Cyclic Diaryl Iodonium Salts: Direct Access to Structurally Diversified Diarylmethane Amides with Potential Neuroprotective and Anticancer Activities

A novel, simple, and high-yielding approach for the preparation of diarylmethane amide derivatives has been developed by reacting cyclic diaryl iodonium salts with nitriles using CuCl as a catalyst. The procedure is efficient with high atom economy and a wide substrate range. Importantly, selective arylation of nitriles was obtained without affecting the phenyl amino/hydroxyl groups. Furthermore, two of the diarylmethane amides (3k, 3s) displayed excellent neuroprotective and anticancer activities.

Copper-Catalyzed One-Pot Synthesis of Dibenzofurans, Xanthenes, and Xanthones from Cyclic Diphenyl Iodoniums

Oxygenation of cyclic diphenyl iodoniums (CDPIs) with varied medium-ring sizes has been fully investigated. This practical copper-catalyzed tandem reaction of CDPIs with water as the oxygen source enables the construction of derivatised dibenzofurans and xanthenes at moderate to good yields. Moreover, structurally important xanthones are also successfully accessed under the oxygenation conditions with additional TEMPO.

Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters

The copper-catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron-deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.

Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water

N-(3-Chloro-2-quinoxalinyl)-N′-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N′-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh3)4 and Pd2(dba)3/PPh3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh3)Cl2] (I) and [Pd(HL2)(PPh3)Cl2] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K2CO3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K2CO3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.

Microwave-promoted palladium catalysed Suzuki cross-coupling reactions of benzyl halides with arylboronic acid

Simple catalytic systems for the coupling of benzyl halides with phenylboronic acid under microwave conditions were tested. Microwave-promoted Suzuki reaction of arylboronic acid with benzyl halides catalysed by PdCl2(PPh3)2 in the mixed solvents DMF/H2O is reported to give diaryl methane derivatives in good to high yield.

Exploration of the structure-activity relationship of the diaryl anilide class of ligands for translocator protein - Potential novel positron emitting tomography imaging agents

A series of novel ligands based on the diaryl anilide (DAA) class of translocator protein (TSPO) ligands was synthesised and evaluated as potential positron emitting tomography (PET) ligands for imaging TPSO in vivo. Fluorine-18 labelling of the molecules was achieved using direct radiolabelling or synthon based labelling approaches. Several of the ligands prepared have promising profiles as potential TSPO PET imaging ligands and will be evaluated further as potential clinical imaging agents.

Palladium-catalyzed decarboxylative coupling of potassium nitrophenyl acetates with aryl halides

A palladium-catalyzed decarboxylative cross-coupling of potassium 2- and 4-nitrophenyl acetates with aryl chlorides and bromides has been developed. Because the nitro group can be readily converted to many other functional groups, the new reaction provides a useful method for the preparation of diverse 1,1-diaryl methanes and their derivatives.

Selective oxidation of aromatic amines to nitro derivatives using potassium iodide-tert-butyl hydroperoxide catalytic system

The direct oxidation of aromatic primary amines to the corresponding nitro compounds selectively in 47-98% yields has been achieved by using potassium iodide as catalyst and tert-butyl hydroperoxide as the external oxidant. The present catalytic system works well for both electron-rich and electron-poor substrates.