1817-77-2

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 2675, 1973 DOI: 10.1021/jo00955a022Synthetic Communications, 24, p. 1999, 1994 DOI: 10.1080/00397919408010207Synthesis, p. 770, 1986 DOI: 10.1055/s-1986-31773

Upstream product

• 100-14-1 4-nitrobenzyl chloride 
• 71-43-2 benzene 
• 619-73-8 4-nitrobenzyl chloride 
• 1144-74-7 4-nitrobenzophenone 
• 101-81-5 Diphenylmethane 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 108-86-1 bromobenzene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 108-88-3 toluene 
• 183156-73-2 N-(4-nitrobenzyl)-N-nitrosoacetamide 
• 98-80-6 phenylboronic acid 
• 7446-70-0 aluminium trichloride 
• 7664-93-9 sulfuric acid 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 

Downstream Products

• 102007-33-0 1,4-bis-(4-nitro-benzyl)-benzene 
• 80213-61-2 4-nitro-4'-(4-nitro-benzyl)-benzophenone 
• 33350-79-7 4-Nitrodiphenyldideuteromethan 
• 80177-27-1 1,2-di(4-nitrophenyl)-1,2-diphenylethane 
• 108-95-2 phenol 
• 62-23-7 4-nitro-benzoic acid 
• 181935-82-0 1-(4-(4-nitrobenzyl)phenyl)ethan-1-one 
• 1144-74-7 4-nitrobenzophenone 
• 1135-12-2 p-benzylaniline 
• 1817-74-9 bis(4-nitrophenyl)methane 
• 1817-75-0 2,4'-dinitrodiphenylmethane 
• 102184-57-6 1,4-bis-(4-nitro-benzoyl)-benzene 
• 122337-23-9 4-benzoylamino-4'-(4-benzoylamino-benzyl)-benzophenone 
• 1313757-12-8 C₁₉H₁₅N₃O₆S 

Relevant academic research and scientific papers

Formation of Acyclic cis-Azobenzene without Light

Reduction mixture of bis(4-nitrobenzyl) ether contained a considerable amount of cis-4,4'-dimethylazobenzene.

Extended scope of in situ iodotrimethylsilane mediated selective reduction of benzylic alcohols

Iodotrimethylsilane, generated in situ from chlorotrimethylsilane and sodium iodide in acetonitrile, selectively reduces moderately electron deficient benzylic alcohols to the analogous toluenes; other reduction sensitive functional groups such as ketone, aldehyde, nitrile, and nitro are unaffected.

Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups

We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.

Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides

Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and h

Dual copper- and photoredox-catalysed C(sp2)-C(sp3) coupling

The use of copper catalysis with visible light photoredox catalysis in a cooperative fashion has recently emerged as a versatile means of developing new C-C bond forming reactions. In this work, dual copper and photoredox catalysis is exploited to effect C(sp2)-C(sp3) cross-couplings between aryl boronic acids and benzyl bromides.

Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions

A novel metal-free process allowing the reductive desulfurization of various benzylic dithioketals to afford diarylmethane and benzylester derivatives with good to excellent yields is reported. At room temperature, this mild reduction process requires only the use of TMSCl and NaI in CH2Cl2 and tolerates a large variety of functional groups. (Figure presented.).

Unmodified Fe3O4 nanostructure promoted with external magnetic field: safe, magnetically recoverable, and efficient nanocatalyst for N- and C-alkylation reactions in green conditions

Transition metal compounds have emerged as suitable catalysts for organic reactions. Magnetic compounds as soft Lewis acids can be used as catalysts for organic reactions. In this report, the Fe3O4 nanostructures were obtained from Fe2+ and Fe3+-salts, under an external magnetic field (EMF) without any protective agent. The X-ray photoelectron spectroscopy, scanning electron microscopy, and energy dispersive X-ray spectroscopy tools were used to characterize these magnetic compounds. The two-dimensional (2-D, it showed nanometric size in the two dimensions, nanorod structure) Fe3O4 compound showed high catalytic activity and stability in N- and C-alkylation reactions. A diverse range of N- and C-alkylation products were obtained in moderate to high yield under green and mild conditions in air. Also the N- and C-alkylation products can be obtained with different selectivity and yield by exposure reactions with EMF. Results of alkylation reactions showed that the presence of Fe(II) and Fe(III) species on the surface of magnetic catalysts (phase structure of magnetic compounds) are essential as very cheap active sites. Also, morphology of magnetic catalysts had influence on their catalytic performances. After the reaction, the catalyst/product(s) separation could be easily achieved with an external magnet and more than 95% of catalyst could be recovered. The catalyst was reused at least four times without any loss of its high catalytic activity for N- and C-alkylation reactions.

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.

Substrate switchable Suzuki-Miyaura coupling for benzyl ester: Vs. benzyl halide

Two reaction conditions were developed to accomplish the substrate switchable Suzuki-Miyaura coupling of benzyl derivatives and arylboronic acid derivatives. Under conditions for esters, benzyl esters such as carbonates and acetates reacted with arylboronic acids to afford the corresponding diarylmethanes. However, the benzyl halides did not react under the same conditions. On the other hand, benzyl halides such as bromides and chlorides furnished diarylmethanes under conditions for halides, under which benzyl ester substrates did not react, in which water was found to play an important role. This switching system was tested using the intermolecular/intramolecular competitive reactions, during which the desired products could be synthesized by selecting the appropriate reaction conditions.

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.