782-92-3

Usage

Uses

Used in Pharmaceutical Industry:
(4-ACETYLPHENYL)PHENYLMETHANE is used as an intermediate in the synthesis of diand triarylmethanes through palladium-catalyzed reductive coupling of N-tosylhydrazones and aryl bromides. These diand triarylmethanes are important compounds with potential applications in the development of pharmaceuticals, particularly as anti-inflammatory, antimicrobial, and antiviral agents.
Used in Chemical Synthesis:
(4-ACETYLPHENYL)PHENYLMETHANE serves as a versatile building block in organic synthesis, allowing for the preparation of a wide range of organic compounds. Its reactivity and functional groups make it suitable for various chemical reactions, such as cross-coupling, oxidation, and reduction, enabling the synthesis of complex molecules with potential applications in various fields, including materials science, agrochemicals, and pharmaceuticals.

Purification Methods

Distil it in a vacuum, then recrystallise it from EtOH (ca 1mL/g). The oxime has m 99.5o (from 60% aqueous EtOH). [Beilstein 7 H 449, 7 III 2176.]

InChI:InChI=1/C15H14O/c1-12(16)15-9-7-14(8-10-15)11-13-5-3-2-4-6-13/h2-10H,11H2,1H3

Upstream product

• 101-81-5 Diphenylmethane 
• 75-36-5 acetyl chloride 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 28493-54-1 benzyltributyltin 
• 350-47-0 1-(4-acetylphenyl)diazonium tetrafluoroborate 
• 100-44-7 benzyl chloride 
• 7446-70-0 aluminium trichloride 
• 591-50-4 iodobenzene 
• 369386-31-2 4-[(2-pyridyldimethylsilyl)methyl]acetophenone 
• 13329-40-3 4-Iodoacetophenone 
• 349611-37-6 [(2-pyridyldimethylsilyl)methyl]benzene 
• 100-39-0 benzyl bromide 
• 6921-34-2 benzylmagnesium chloride 
• 65189-90-4 4-(1-hydroxyethyl)benzophenone 

Downstream Products

• 1135-12-2 p-benzylaniline 
• 65189-90-4 4-(1-hydroxyethyl)benzophenone 
• 28179-31-9 1-(4-benzylphenyl)-2-bromoethanone 
• 750637-50-4 1,3,5-tris-(4-benzyl-phenyl)-benzene 
• 90811-58-8 4'-benzyl-trans-chalcone 
• 18908-74-2 ethyl 4-benzylbenzoate 
• 38110-22-4 (E)-3-(4-Benzyl-phenyl)-but-2-enoic acid methyl ester 
• 18915-92-9 4-Benzylcyclohexancarbonsaeure (trans) 
• 93731-54-5 1-(α-Methyl-4-benzyl-benzyl)-2-methoxycarbonyl-hydrazin 
• 215368-61-9 [4-(2-indolyl)phenyl]phenylmethane 
• 15866-31-6 phenyl(p-vinylphenyl)methane 
• 620-85-9 1-benzyl-4-ethylbenzene 
• 38110-21-3 (E)-3-(4-Benzyl-phenyl)-but-2-enoic acid 
• 18908-90-2 C₄₀H₃₈O₄ 

Relevant academic research and scientific papers

Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes

Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.

Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**

Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.

Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides

The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

A general copper-catalyzed radical C(sp3)?C(sp2) cross-coupling to access 1,1-diarylalkanes under ambient conditions

A general copper-catalyzed C(sp3)?C(sp2) cross-coupling of (hetero)benzyl bromides with the air- and moisture-stable aryl nucleophiles has been developed, providing a facile access to pharmaceutically useful 1,1-di(hetero)arylalkane and 1-aryl-1-heteroarylalkane scaffolds. Critical to the success is the utilization of a proline-based N,N,P-ligand to enhance the reducing capability of copper, thus easily converting benzyl bromides to the corresponding radical species via a single-electron transfer process under ambient conditions. The reaction features a broad substrate scope, covering (hetero)arylboronate esters, oxadiazoles, and benzo[d]oxazoles, as well as primary and secondary (hetero)benzyl bromides with excellent functional group tolerance.

Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst

The synergistic combination of a heterogeneous organic semiconductor mesoporous graphitic carbon nitride (mpg-CN) and a homogeneous nickel catalyst with visible-light irradiation at room temperature affords the C(sp2)-C(sp3) cross-co

Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate

The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excitation of a boracene-based alkylborate. This system is based on the photophysical properties of the organoboron molecule. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond formations such as alkyl-aryl cross-coupling or vicinal alkylarylation of alkenes, enabling the introduction of various C(sp3) fragments to organic molecules.

Remote Nickel-Catalyzed Cross-Coupling Arylation via Proton-Coupled Electron Transfer-Enabled C-C Bond Cleavage

Cross-coupling reactions for carbon-carbon and carbon-heteroatom bond formation are of great importance in modern chemical synthesis. In addition to classical cross-couplings involving preformed or preactivated coupling partners, more recently breakthroughs have been made in the selective, direct coupling of abundant aliphatic carbon-hydrogen bonds using hydrogen atom transfer reactions in which the bond-dissociation energy is the thermodynamic driving force. The more challenging carbon-carbon bond activation is still rather underdeveloped due to the bond inertness. Herein, we report a mild and general strategy for the activation of a diverse set of readily available cyclic alcohols for the remote and site-specific arylation of ketones via the combination of photoredox-mediated multisite concerted proton-electron transfer (MS-PCET) and nickel catalysis. The current cross-coupling proceeds with the generation of an alkoxy radical utilizing bond-dissociation free energy (BDFE) as the thermodynamic driving force. Subsequently, the resulting remote carbon-centered radicals formed by C-C cleavage merge with the nickel catalytic cycle to create the challenging C(sp3)-C(sp2) bonds.

Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C-H bonds

Convergent paired electrosynthesis is an energy-efficient approach in organic synthesis; however, it is limited by the difficulty to match the innate redox properties of reaction partners. Here we use nickel catalysis to cross-couple the two intermediates

Visible Light-Catalyzed Benzylic C-H Bond Chlorination by a Combination of Organic Dye (Acr+-Mes) and N-Chlorosuccinimide

By combining "N-chlorosuccinimide (NCS)"as the safe chlorine source with "Acr+-Mes"as the photocatalyst, we successfully achieved benzylic C-H bond chlorination under visible light irradiation. Furthermore, benzylic chlorides could be converted to benzylic ethers smoothly in a one-pot manner by adding sodium methoxide. This mild and scalable chlorination method worked effectively for diverse toluene derivatives, especially for electron-deficient substrates. Careful mechanistic studies supported that NCS provided a hydrogen abstractor "N-centered succinimidyl radical,"which was responsible for the cleavage of the benzylic C-H bond, relying on the reducing ability of Acr?-Mes.