5739-39-9

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 97, 1989 DOI: 10.1080/00397918908050957

InChI:InChI=1/C15H13ClO/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-7,9-10H,8,11H2

Upstream product

• 52085-96-8 3-(4-chlorophenyl)propanoyl chloride 
• 71-43-2 benzene 
• 98-86-2 acetophenone 
• 873-76-7 para-Chlorobenzyl alcohol 
• 123558-66-7 (Z)-3-(4-Chloro-phenyl)-2-methanesulfonyl-1-phenyl-propenone 
• 7664-93-9 sulfuric acid 
• 859189-07-4 2-(4-chlorobenzyl)-3-oxo-3-phenylpropionic acid ethyl ester 
• 34544-99-5 2-Benzenesulfonyl-3-(4-chloro-phenyl)-1-phenyl-propan-1-one 
• 123558-70-3 3-(4-Chloro-phenyl)-2-methanesulfonyl-1-phenyl-propan-1-one 
• 75400-53-2 9-[2-(4-Chloro-phenyl)-ethyl]-9-bora-bicyclo[3.3.1]nonane 
• 380451-93-4 thiobenzoic acid S-(2-morpholin-4-yl-2-oxo-ethyl) ester 
• 38895-95-3 p-chlorochalcone dibromide 
• 104-88-1 4-chlorobenzaldehyde 
• 1073-67-2 4-vinylbenzyl chloride 

Downstream Products

• 854867-66-6 3-(4-chloro-benzyl)-2-phenyl-quinoline-4-carboxylic acid 
• 113478-79-8 2-bromo-3-(4-chlorophenyl)-1-phenylpropane-1-one 
• 1180676-62-3 ethyl 5-(4-chlorophenyl)-3-phenylpent-2-enoate 
• 1180676-61-2 ethyl 5-(4-chlorophenyl)-3-phenylpent-2-enoate 
• 1180676-32-7 PS 48 
• 24721-26-4 4-chlorochalcone 
• 93-89-0 benzoic acid ethyl ester 
• 1402229-05-3 4-((4-amino-5-benzoyl-6-(4-chlorophenyl)-2-morpholinopyridin-3-yl)diazenyl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one 
• 1221963-27-4 (Z)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile 
• 1221963-28-5 (E)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile 
• 113530-94-2 2-(4-Chloro-benzyl)-3-phenyl-1,2-dihydro-quinoxaline 

Relevant academic research and scientific papers

Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite

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BTP-Rh@g-C3N4 as an efficient recyclable catalyst for dehydrogenation and borrowing hydrogen reactions

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Nickel-catalyzed α-alkylation of ketones with benzyl alcohols

We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.

SmI2-mediated C-alkylation of Ketones with Alcohols under Microwave Conditions: A Novel Route to Alkylated Ketones

A novel protocol is developed towards the preparation of alkylated ketones from alcohols in presence of catalytic amount of SmI2 and base with the elimination of water as a single by-product under microwave irradiation conditions. Furthermore, applicability of this methodology to the synthesis of Donepezil and late-stage functionalization in Pregnenolone is also reported. Successful application of this methodology in Friedl?nder quinolone synthesis using 2-aminobenzyl alcohol and various acetophenones expand the synthetic utility of this protocol.

A Proton-Responsive Pyridyl(benzamide)-Functionalized NHC Ligand on Ir Complex for Alkylation of Ketones and Secondary Alcohols

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Cu(I) mediated hydrogen borrowing strategy for the α-alkylation of aryl ketones with aryl alcohols

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Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines

Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.

Unveiling the catalytic nature of palladium-N-heterocyclic carbene catalysts in the α-alkylation of ketones with primary alcohols

We report herein the synthesis of four new Pd-PEPPSI complexes with backbone-modified N-heterocyclic carbene (NHC) ligands and their application as catalysts in the α-alkylation of ketones with primary alcohols using a borrowing hydrogen process and tandem Suzuki-Miyaura coupling/α-alkylation reactions. Among the synthesized Pd-PEPPSI complexes, complex2chaving 4-methoxyphenyl groups at the 4,5-positions and 4-methoxybenzyl substituents on the N-atoms of imidazole exhibited the highest catalytic activity in the α-alkylation of ketones with primary alcohols (18 examples) with yields reaching up to 95%. Additionally, complex2cwas demonstrated to be an effective catalyst for the tandem Suzuki-Miyaura-coupling/α-alkylation of ketones to give biaryl ketones with high yields. The heterogeneous nature of the present catalytic system was verified by mercury poisoning and hot filtration experiments. Moreover, the formation of NHC-stabilized Pd(0) nanoparticles during the α-alkylation reactions was identified by advanced analytical techniques.

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.