54197-71-6

Upstream product

• 52085-97-9 3-(2-chlorophenyl)propionyl chloride 
• 71-43-2 benzene 
• 22966-11-6 (2E)-3-(2-chlorophenyl)-1-phenylprop-2-en-1-one 
• 1643-28-3 3-(2-chlorophenyl)propanoic acid 
• 1794-45-2 (E)-3-(2-chlorophenyl)propenal 
• 98-80-6 phenylboronic acid 
• 2039-87-4 2-chlorostyrene 
• 65-85-0 benzoic acid 
• 98-85-1 1-Phenylethanol 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 89-98-5 2-chloro-benzaldehyde 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 54197-70-5 N-[3-(2-chlorophenyl)-1-phenyl-1-propylidene]-4-anisidine 

Relevant academic research and scientific papers

Photoredox-Catalyzed Hydroacylation of Olefins Employing Carboxylic Acids and Hydrosilanes

A hydroacylation reaction of alkenes has been achieved employing readily available carboxylic acids as the acyl source and hydrosilanes as a hydrogen source via photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps has dramatically expanded new applications of carboxylic acids in organic synthesis. The protocol also features extremely mild conditions, broad substrate scope, and good functional group tolerance, affording a novel and convenient approach to hydroacylation of alkenes.

Synthesis of α-Alkylated Ketones via Selective Epoxide Opening/Alkylation Reactions with Primary Alcohols

A new method for converting terminal epoxides and primary alcohols into α-alkylated ketones under borrowing hydrogen conditions is reported. The procedure involves a one-pot epoxide ring opening and alkylation via primary alcohols in the presence of an N-heterocyclic carbene iridium(I) catalyst, under aerobic conditions, with water as the side product.

C-C coupling formation using nitron complexes

A series of RuII (1), RhIII (2), IrIII (3, 4), IrI (5) and PdII (6-9) complexes of the 'instant carbene' nitron were prepared and characterized by 1H- and 13C-NMR, FT-IR and elemental analysis. The molecular structures of complexes 1-4 and 6 were determined by X-ray diffraction studies. The catalytic activity of the complexes (1-9) was evaluated in alpha(α)-alkylation reactions of ketones with alcohol via the borrowing hydrogen strategy under mild conditions. These complexes were able to perform this catalytic transformation in a short time with low catalyst and base amounts under an air atmosphere. Also, the PdII-nitron complexes (6-9) were applied in the Suzuki-Miyaura C-C coupling reaction and these complexes successfully initiated this reaction in a short time (30 minutes) using the H2O/2-propanol (1.5?:?0.5) solvent system. The DFT calculations revealed that the Pd0/II/0 pathway was more preferable for the mechanism

Synthesis and catalytic applications of Ru and Ir complexes containing N,O-chelating ligand

A series of monometallic complexes (Ru1–3, Ir1–3) which have N,O-chelating ligand (pyrazine-2-carboxylate (1), pyridine-2-carboxylate (2), quinoline carboxylate(3) and bimetallic complexes (Ru4,5, Ir4,5) bridged by pyrazine-2,3- dicarboxylate (4) and imidazole-4,5-dicarboxylate(5) were synthesized and characterized by 1H-, 13C NMR, FT-IR, and elemental analysis. The crystal structure of Ir2 was determined by X-ray crystallography. The complexes (Ru1–5, Ir1–5) were applied to investigate the electronic and steric effect of ligand in their catalytic activities in transfer hydrogenation and alpha(α)-alkylation reaction of ketones with alcohols. The activities of iridium complexes (Ir1–5) were much more efficient than ruthenium complexes (Ru1–5). The highest activity for both reactions was observed for the complex (Ir2) with pyridine-2-carboxylate. The Ir hydride species was monitored for both reactions.

Electrochemical 1,4-reduction of α,β-unsaturated ketones with methanol and ammonium chloride as hydrogen sources

A sustainable, chemoselective 1,4-reduction of α,β-unsaturated ketones by means of an electrochemical method is presented, wherein the extremely inexpensive ammonium chloride (NH4Cl) is applied as the only additive. The reaction proceeds smoothly in the air at ambient temperature. Mechanistic studies reveal that both NH4Cl and solvent methanol work as hydrogen donors.

Photocatalytic decarboxylative coupling between α-oxocarboxylicacids and alkenes

Photocatalytic decarboxylative cross-coupling which achieves the derivatization of widespread organic acids has become a hot topic in organic synthesis. As special acids, α-oxocarboxylicacids show the great potential in running decarboxylation to construc

Ruthenium-Catalyzed β-Alkylation of Secondary Alcohols and α-Alkylation of Ketones via Borrowing Hydrogen: Dramatic Influence of the Pendant N-Heterocycle

Three bidentate ruthenium(II) complexes with a pyridonate fragment were prepared and fully characterized. These complexes are structurally similar, but differ in their pendant substituents. Complex 1 contains a phenyl unit, whereas complexes 2 and 3 have uncoordinated thienyl and thiazolyl groups, respectively. These complexes were tested as catalysts for β-alkylation of secondary alcohols with primary alcohols, and 3 shows the highest activity, suggesting the thiazolyl ring participates in the catalytic process. Furthermore, 3 is an excellent catalyst for α-alkylation of ketones with primary alcohols. Various α-alkylated ketones were synthesized in high yields, by using 0.05 mol % 3 and 0.25 equiv of t-BuOK within 30 min.

Unusual C-O bond cleavage of aromatic ethers in ruthenium complexes bearing a 2-alkoxypyridyl fragment

Two tetradentate (NNOP) ruthenium products [{RO-C5H3N-C5H3N-CH(O)-C6H4-PPh2}Ru(CO)(PPh3)]Cl (1: R = Me; 3: R = Ph) were isolated by the reactions of the corresponding ligands with RuHCl(PPh3)3(CO). Complex 1 could also be transformed into 2 when heated in THF, through C-OMe bond cleavage. The mechanism of the unusual C-O cleavage in complex 1 was investigated, and the results indicate that it is an SN2 mechanism through the attack of trace amounts of neutral H2O. In contrast, in the presence of KOH, the reaction switches to an SNAr chemistry. The bidentate ruthenium isomers [{CH3O-C5H3N-C5H4N}RuH(CO)(PPh3)2]Cl (4a and 4b) could undergo similar C-O cleavage, affording product {O-C5H3N-C5H4N}RuH(CO)(PPh3)2 (5), which reacted with HCl to generate complex [{HO-C5H3N-C5H4N}RuH(CO)(PPh3)2]Cl (6). These complexes were tested as catalysts for β-alkylation of secondary alcohols with primary alcohols, and a series of β-alkylated 1-phenylethanol derivatives were isolated in high yields.

Piano-stool Ru (II) arene complexes that contain ethylenediamine and application in alpha-alkylation reaction of ketones with alcohols

A series of piano-stool Ru (II) complexes (Ru1–7) bearing ethylenediamine with aryl and aliphatic groups were prepared and fully characterized by 1H, 13C, 19F and 31P NMR spectroscopy, FT-IR and elemental analysis. The crystal structures of Ru2–4 and Ru7 were determined by X-ray crystallography. They were successfully applied to the alpha(α)-alkylation of aliphatic and aromatic ketones with alcohols via the borrowing hydrogen strategy in mild reaction conditions within a short time. The catalytic system has a broad substrate scope, which allows the synthesis of alpha alkylated ketones with excellent yields. The electronic and steric effects of complexes on catalytic activity were analysed. The influence of the carbon chain length of the ligand on the alpha-alkylation reaction of ketones was also investigated. The catalytic cycle was also examined by 1H-NMR spectroscopy in d8-toluene.

The α-alkylation of ketones with alcohols in pure water catalyzed by a water-soluble Cp?Ir complex bearing a functional ligand

A water-soluble dinuclear Cp?Ir complex bearing 4,4′,6,6′-tetrahydroxy-2,2′-bipyrimidine as a bridging ligand was found to be a highly effective catalyst for the α-alkylation of ketones with alcohols in pure water. In the presence of catalyst (0.5 mol%), a series of desirable products were obtained with high reaction economy under environmentally benign conditions. The importance of the hydroxy group in the ligand for catalytic hydrogen transfer was confirmed by mechanism experiments. Furthermore, the application of this catalytic system for the synthesis of a biologically active molecule donepezil in pure water has been accomplished. Notably, this research would facilitate the progress of C-C bond-forming reactions in water catalyzed by water-soluble metal-ligand bifunctional catalysts.