898767-89-0

Usage

InChI:InChI=1/C16H15FO/c1-12-2-7-14(8-3-12)16(18)11-6-13-4-9-15(17)10-5-13/h2-5,7-10H,6,11H2,1H3

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 122-00-9 para-methylacetophenone 
• 1481-32-9 6-fluoroindan-1-one 
• 4463-41-6 2-(p-tolyl)-1,3,2-dioxaborinane 
• 459-56-3 4-fluorobenzylic alcohol 
• 13565-38-3 (E)-3-(4-fluorophenyl)-1-(p-tolyl)prop-2-en-1-one 
• 67-56-1 methanol 
• 13565-38-3 3-(4-fluorophenyl)-1-p-tolylprop-2-en-1-one 
• 109-77-3 malononitrile 

Downstream Products

• 13565-38-3 3-(4-fluorophenyl)-1-p-tolylprop-2-en-1-one 

Relevant academic research and scientific papers

Suzuki-Miyaura coupling of simple ketones via activation of unstrained carbon-carbon bonds

Here, we describe that simple ketones can be efficiently employed as electrophiles in Suzuki-Miyaura coupling reactions via catalytic activation of unstrained C-C bonds. A range of common ketones, such as cyclopentanones, acetophenones, acetone and 1-indanones, could be directly coupled with various arylboronates in high site-selectivity, which offers a distinct entry to more functionalized aromatic ketones. Preliminary mechanistic study suggests that the ketone α-C-C bond was cleaved via oxidative addition.

Phosphine-Free NNN-Manganese Complex Catalyzed α-Alkylation of Ketones with Primary Alcohols and Friedl?nder Quinoline Synthesis

Herein, we report a very simple and inexpensive catalytic system based on Earth's abundant transition metal manganese and on a bench-stable phosphine-free NNN-pincer ligand for an atom-efficient α-alkylations of ketones with primary alcohols via hydrogen-autotransfer C?C bond formation protocol. The precatalyst could be generated in situ and could be activated by using catalytic amount of base under milder conditions. A range of ketones were efficiently diversified with a broad range of primary alcohols in good to excellent isolated yields. Remarkably, this catalyst could also be employed for the synthesis of quinoline derivatives using 2-aminobenzyl alcohol as an alkylating agent. The later reaction is highly benign producing only hydrogen and water as byproducts. (Figure presented.).

Isolation and Characterization of Regioisomers of Pyrazole-Based Palladacycles and Their Use in α-Alkylation of Ketones Using Alcohols

Regioisomers of 3,5-diphenyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-based palladacycles (1 and 2) were synthesized by the aromatic C-H bond activation of N/3-aryl ring. The application of these regioisomers as catalysts to enable the formation of α-alkylated ketones or quinolines with alcohols using a hydrogen borrowing process is evaluated. Experimental results reveal that palladacycle 2 is superior over palladacycle 1 to catalyze the reaction under similar reaction conditions. The reaction mechanisms for the palladacycles 1 and 2 catalyzed α-alkylation of acetophenone were studied using density functional theoretical (DFT) methods. The DFT studies indicate that palladacycle 2 has an energy barrier lower than that of palladacycle 1 for the alkylation reaction, consistent with the better catalytic activity of palladacycle 2 seen in the experiments. The palladacycle-phosphine system was found to tolerate a wide range of functional groups and serves as an efficient protocol for the synthesis of α-alkylated products under solvent-free conditions. In addition, the synthetic protocol was successfully applied to prepare donepezil, a drug for Alzheimer's disease, from simple starting materials.

RhCl(CO)(PPh3)2 catalyzed α-alkylation of ketones with alcohols

A simple and efficient method for α-alkylation of ketones with primary alcohols catalyzed by RhCl(CO)(PPh3)2 without additional additives under mild conditions is developed. It has a wide substrate scope, high atom-efficiency and chemoselectivity. It is an environmentally friendly method to build C[sbnd]C bond because water is the only byproduct.

Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the SRN1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

Synthesis of polysubstituted pyridines under combined microwave and ultrasound irradiation: K2CO3-promoted tandem addition/cyclization/hydrogen shift process

A convenient and efficient K2CO3-promoted tandem reaction of chalcone, malononitrile, and methanol for the synthesis of highly functionalized pyridines has been developed. This multi-component reaction employing the weak nucleophilic agent methanol proceeded smoothly under combined microwave and ultrasound irradiation (CMUI). The reaction mechanism was proposed to consist of a Michael addition, a methoxylation of CN bond, a cyclization to a 1,4-dihydropyridine and an intermolecular hydrogen shift between 1,4-dihydropyridine and initial chalcone.

Selective 1,4-reduction of chalcones with Zn/NH4Cl/C 2H5OH/H2O

In this paper, the Zn/NH4Cl/C2H5OH/H 2O system was applied for the selective 1,4-reduction of chalcones undermild conditions with high selectivity. Themerit lies in inexpensive reagent, simple operation and envi