842-08-0

Upstream product

• 3800-06-4 2-amino-4'-fluorobenzophenone 
• 108-24-7 acetic anhydride 
• 120303-62-0 (4-fluorophenyl)(2-nitrophenyl)methanone 
• 610-14-0 2-nitrobenzyl chloride 
• 19591-17-4 o-iodoacetanilide 
• 459-57-4 4-fluorobenzaldehyde 
• 103-84-4 Acetanilid 
• 459-56-3 4-fluorobenzylic alcohol 
• 62-53-3 aniline 
• 352-32-9 p-fluorotoluene 
• 552-16-9 ortho-nitrobenzoic acid 

Downstream Products

• 105189-03-5 2-[4-(3-hydroxypropyl)-1-piperazinyl]-4-(4-fluorophenyl)quinoline 
• 105188-98-5 2-[4-(2-hydroxyethyl)-1-piperazinyl]-4-(4-fluorophenyl)quinoline dihydrochloride 
• 105189-06-8 2-(4-Ethyl-piperazin-1-yl)-4-(4-fluoro-phenyl)-quinoline; hydrochloride 
• 120301-22-6 4-(4-Fluoro-phenyl)-2-(4-methyl-piperazin-1-yl)-quinoline; hydrochloride 
• 120301-18-0 2-(4-Benzyl-piperazin-1-yl)-4-(4-fluoro-phenyl)-quinoline 
• 120301-16-8 2-(1-piperazinyl)-4-(4-fluorophenyl)quinoline 
• 105189-21-7 2-chloro-4-(4-fluorophenyl)quinoline 
• 106015-75-2 4-(4-fluorophenyl)quinolin-2(1H)-one 

Relevant academic research and scientific papers

Study of Lewis acid accelerated palladium catalyzed C[sbnd]H activation

Acceleration of palladium catalyzed C[sbnd]H activation by various Lewis Acids was demonstrated on the directed ortho-alkenylation and acylation of acetanilide and urea derivatives. The universality of this effect was investigated by the study of differen

Palladium Catalyzed Direct Acylation of Iodo-Acetanilides/Iodo-Phenyl Acetates: Domino One-Pot Synthesis of 2-Quinolinones

Pd-catalyzed direct acylation reaction of iodoacetanilides/iodophenyl acetates with aldehydes is presented. Simple, bench-top aldehydes were used as non-toxic acylating agents. This protocol comprises direct coupling with aldehydes without activating the carbonyl group and without directing group assistance. The strategy was applied to a domino one-pot synthesis of 2-quinolinones through acylation and intramolecular aldol condensation. Significantly, the strategy was extended to the domino one-pot synthesis of drugs and bioactive compounds.

Activation of C-H Activation: The Beneficial Effect of Catalytic Amount of Triaryl Boranes on Palladium-Catalyzed C-H Activation

Herein we report a novel approach to the acceleration of palladium-catalyzed C-H activation reactions. We demonstrated that the utilization of electron-deficient triaryl boranes as Lewis acidic cocatalysts of palladium enables the directed cross dehydrogenative coupling of aldehydes and anilides under mild reaction conditions. Study of the kinetic profile of the transformation reveals a unique, unexpectedly long induction period of the transformation.

Palladium-catalyzed C-H bond acylation of acetanilides with benzylic alcohols under aqueous conditions

Palladium-catalyzed dehydrogenative coupling reactions between acetanilides and benzylic alcohols under aqueous conditions are reported. A wide range of benzophenone derivatives could be obtained in good to excellent yields up to 98 %. Mechanism studies showed that a bimetallic palladium cyclopalladated complex might be involved in the catalysis.

Dual role of acetanilides: Traceless removal of a directing group through deacetylation/diazotation and palladium-catalyzed C-C-coupling reactions

The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.

A one-pot process for palladium catalyzed direct C-H acylation of anilines in water using a removable ortho directing group

A new mild, practical method for the synthesis of aminobenzophenone derivatives through a three step one-pot reaction sequence involving acylation of anilines, palladium catalyzed cross-dehydrogenative coupling of the formed anilides and the hydrolytic cleavage is reported. The full reaction sequence was performed under aqueous conditions.

Mild palladium-catalyzed oxidative direct ortho-C-H acylation of anilides under aqueous conditions

Palladium-catalyzed cross-dehydrogenative coupling between anilides and aromatic aldehydes was achieved under aqueous conditions. A wide variety of the desired benzophenone derivatives was isolated in good to excellent yield. The reaction rate acceleration effect of acid and detergent has been demonstrated. Mechanistic insight has been obtained from quantum chemical calculations. Copyright

Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C-H bond acylation of acetanilides

A palladium-catalyzed cascade cross-coupling of acetanilide and toluene for the synthesis of ortho-acylacetanilide is described. Toluene derivatives can act as effective acyl precursors (upon sp3-C-H bond oxidation by a Pd/TBHP system) in the oxidative coupling between two C-H bonds. This dehydrogenative Pd-catalyzed ortho-acylation proceeds under mild reaction conditions.

Palladium-catalyzed ortho-acylation of acetanilides with aldehydes through direct Ci-H bond activation

Easy access to o-acyl acetanilides: A new Pd-catalyzed ortho-acylation of acetanilides with both aromatic and aliphatic aldehydes has been developed based on a Ci-H activation process. In the presence of tert-butyl hydroperoxide (TBHP) as the ideal oxidant, this reaction provides an efficient access to ortho-acyl acetanilides in good yields (see scheme). Copyright

Palladium-catalyzed oxidative C-H bond coupling of steered acetanilides and aldehydes: A facile access to ortho -acylacetanilides

A palladium-catalyzed oxidative C-H bond functionalization/ortho-acylation of acetanilides using easily accessible aldehyde as the acyl source is described. In the presence of a Pd(TFA)2 catalyst and tert-butylhydroperoxide at 90 °C in general, an array of ortho-acylacetanilides can be afforded in good yields.