2069-48-9

Usage

Chemical Properties

white crystal powder

InChI:InChI=1/C13H8ClFO/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8H

Upstream product

• 403-43-0 4-fluorobenzoyl chloride 
• 108-90-7 chlorobenzene 
• 462-06-6 fluorobenzene 
• 122-01-0 4-chloro-benzoyl chloride 
• 1033-26-7 4,4'-dinitrobenzophenone 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 106-39-8 bromochlorobenzene 
• 1765-93-1 4-fluoroboronic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 39769-26-1 (E)-1-(4-fluorophenyl)-2-(4-chlorophenyl)ethene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 352-34-1 4-fluoro-1-iodobenzene 
• 201230-82-2 carbon monoxide 
• 21700-74-3 (p-chlorophenyl)triethoxysilane 

Downstream Products

• 2795-76-8 4-chloro-α-(4-fluorophenyl)benzenemethanol 
• 122601-83-6 (4-Chloro-phenyl)-(4-imidazol-1-yl-phenyl)-methanone 
• 93765-34-5 (4-Chloro-phenyl)-(4-fluoro-phenyl)-pyrimidin-5-yl-methanol 
• 42019-78-3 4-chloro-4'-hydroxybenzophenone 
• 29558-88-1 4-chlorobenzoic acid 4-fluorophenyl ester 
• 3794-41-0 4-Fluor-benzoesaeure-<4-chlor-phenylester> 
• 371-41-5 4-Fluorophenol 
• 456-22-4 4-Fluorobenzoic acid 
• 106-48-9 4-chloro-phenol 
• 74-11-3 para-chlorobenzoic acid 
• 812685-06-6 2-(4-chlorophenyl)-2-(4-fluorophenyl)-1,3-dioxolane 
• 123853-75-8 3,6-bis-(4'-(4''-chlorobenzoyl)phenoxy)xanthone 
• 389634-34-8 4,4'-bis[4''-(4'''-chlorobenzoyl)phenoxy](hexafluoroisopropylidene)dibenzene 
• 1346939-72-7 (4'-butylbiphenyl-4-yl)(4'-(dimethylamino)biphenyl-4-yl)methanone 

Relevant academic research and scientific papers

AIBN initiated functionalization of the benzylic sp3 C[sbnd]H and C[sbnd]C bonds in the presence of dioxygen

A sp3 C[sbnd]H bond functionalization and C[sbnd]C bond cleavage were realized by AIBN/O2 catalyst system, providing a series of benzophenones under mild reaction conditions. The mechanistic study shows that a peroxide intermediate is involved in this transformation, and in the case of diphenylmethanes, the sp3 C[sbnd]C bond is cleaved through the peroxide rearrangement, which might provides a new way to cleave relatively strong C[sbnd]C bond and be applied to more general C[sbnd]C bond activation.

Palladium-Catalyzed Amide N-C Hiyama Cross-Coupling: Synthesis of Ketones

N-Acylglutarimides and arylsiloxanes reacted in the presence of Pd(OAc)2/PCy3, Et3N·3HF, and LiOAc to provide the corresponding arylketones in good yields. Aryl-, vinyl-, and alkyl-substituted N-acylglutarimides showed good activity in the coupling reactions of arylsiloxanes. The reaction had a broad substrate scope and showed good functional group tolerance. N-Benzoylsuccinimide and N-protected N-phenylbenzamides showed good activities in coupling reactions with phenylsiloxane. The employment of CuF2 as an activor afforded the decarbonylative products at 160 °C.

Photo-nickel dual catalytic benzoylation of aryl bromides

The dual catalytic arylation of aromatic aldehydes by aryl bromides using UV-irradiation and a nickel catalyst is reported. The reaction product serves as a photocatalyst and a hydrogen atom transfer agent for this transformation.

A Dendralenic C-H Acid

The design and synthesis of a strong, dendralenic C-H acid is described. Crystal structure analyses confirm the proposed structure. Despite the moderate stability of our motif, an application to Bronsted acid catalysis has been explored.

Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of Arylboronic Acids and α-Iminonitriles through C–CN Bond Activation

A Pd-catalyzed Suzuki–Miyaura cross-coupling reaction between arylboronic acids and α-iminonitriles has been developed. The reaction proceeds through selective activation of the C–CN bond, tolerates a wide range of substituents, and delivers the versatile ketone products in moderate to excellent yields.

A general approach to intermolecular carbonylation of arene C-H bonds to ketones through catalytic aroyl triflate formation

The development of metal-catalysed methods to functionalize inert C-H bonds has become a dominant research theme in the past decade as an approach to efficient synthesis. However, the incorporation of carbon monoxide into such reactions to form valuable ketones has to date proved a challenge, despite its potential as a straightforward and green alternative to Friedel-Crafts reactions. Here we describe a new approach to palladium-catalysed C-H bond functionalization in which carbon monoxide is used to drive the generation of high-energy electrophiles. This offers a method to couple the useful features of metal-catalysed C-H functionalization (stable and available reagents) and electrophilic acylations (broad scope and selectivity), and synthesize ketones simply from aryl iodides, CO and arenes. Notably, the reaction proceeds in an intermolecular fashion, without directing groups and at very low palladium-catalyst loadings. Mechanistic studies show that the reaction proceeds through the catalytic build-up of potent aroyl triflate electrophiles.

1,1,3,3-Tetratriflylpropene (TTP): A Strong, Allylic C–H Acid for Br?nsted and Lewis Acid Catalysis

Tetratrifylpropene (TTP) has been developed as a highly acidic, allylic C–H acid for Br?nsted and Lewis acid catalysis. It can readily be obtained in two steps and consistently shows exceptional catalytic activities for Mukaiyama aldol, Hosomi–Sakurai, an

Transition metal-free Suzuki type cross-coupling reaction for the synthesis of dissymmetric ketones

A simple, efficient and metal-free route for the synthesis of dissymmetric ketones through Suzuki type cross-coupling reaction has been established. This strategy signifies an attractive, cost-effective and operationally convenient tool for the synthesis of a wide range of dissymmetric ketones. Although conventional routes for the synthesis of ketones have been widely used, the potential challenge with these methods is functional group tolerance. The reported metal-free method represents a reaction with moderate functional group tolerance. The procedure is operationally convenient and shows broad substrate scope with good to excellent product yields.

A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents

The Suzuki–Miyaura cross-coupling (SMC) reactions of several heteroaryl chlorides, benzyl chlorides, and aryl acid chlorides with (hetero)arylboron reagents have been investigated in the presence of [Pd(HL1)(PPh3)Cl2] (I) [HL1 = 3-[(2,6-diisopropylphenyl)-1-imidazolio]-2-quinoxalinide] as catalyst and K2CO3 as base in neat water. The synthesis of the heterocycle-containing biaryls required the addition of 2 mol-% of a phosphine ligand (PPh3 or X-Phos). A combination of more than 115 substrates were screened and it was found that I is a versatile catalyst that can produce heterocycle-containing biaryls, diarylmethanes, and benzophenones in moderate-to-excellent yields.

Synthesis of a polar phosphinoferrocene amidosulfonate ligand and its application in pd-catalyzed cross-coupling reactions of aromatic boronic acids and acyl chlorides in an aqueous medium

The reaction of [1′-(diphenylphosphino)ferrocenyl]methylamine (1), generated in situ from its hydrochloride and triethylamine, with 2-sulfobenzoic anhydride afforded an anionic phosphino-amide, which was isolated as a triethylammonium salt, Ph2PfcCH2NHCOC6H4SO3(HNEt3) (2; fc = ferrocene-1,1′-diyl). A similar reaction of 1 with phthalic anhydride only furnished the salt (Ph2PfcCH2NH3)[C6H4CO2H(CO2)]. When it was reacted with [PdCl2(MeCN)2] and [LNCPd(μ-Cl)]2 (LNC = 2-[(dimethylamino-κN)methyl]phenyl-κC1), compound 2 gave rise to the bis-phosphine complex [PdCl2(2-κP)2] and the bridge-cleavage product [LNCPdCl(2-κP)], respectively. An analogue of the latter complex containing 2′-amino-[1,1′-biphenyl]-2-yl-κ2N,C2 as the auxiliary chelating ligand, compound 8, was prepared in a similar manner from 2 and the respective Pd precursor. Finally, the reaction of 2 with [LNCPd(acac)] proceeded with the replacement of the acetylacetonate ligand (acac), affording a dipalladium complex featuring two phosphinosulfonate anions as the O,P-bridges, [LNCPd(μ(P,O)-Ph2PfcCH2NHCOC6H4SO3)]2, which was structurally characterized by single-crystal X-ray diffraction analysis. All of these Pd(II) complexes, especially compound 8, formed active catalysts for Pd-mediated cross-coupling of aromatic boronic acids with benzoyl chlorides to produce substituted benzophenones in toluene (benzene)-water biphasic mixtures. This particular coupling reaction was employed during the preparation of 4′-chloro-4-hydroxybenzophenone, which was in turn converted to fenofibrate, a generic drug widely used to reduce cholesterol levels in blood.