75116-29-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 154386-63-7 N-(2-iodophenyl)-N-methylmethacrylamide 
• 15796-89-1 N-methyl-N-phenylmethacrylamide 
• 7099-91-4 p-methoxybenzoylformic acid 
• 105-13-5 4-Methoxybenzyl alcohol 
• 1611-83-2 2-methyl-N-phenylacrylamide 
• 62-53-3 aniline 
• 4254-17-5 4-methoxybenzoin 
• 22711-21-3 4-methoxybenzil 
• 100-09-4 4-methoxybenzoic acid 
• 794-94-5 p-Methoxybenzoic anhydride 
• 1027513-97-8 2,2-difluoro-2-(4-methoxyphenyl)acetic acid 
• 112545-98-9 2,2-difluoro-2-(4-methoxyphenyl)acetic acid ethyl ester 
• 696-62-8 para-iodoanisole 

Relevant academic research and scientific papers

Diversity-oriented syntheses: Coupling reactions between electron-deficient olefins and aryl aldehydes via C(sp2)-H functionalization

A diversity-oriented syntheses by coupling three electron-deficient olefins (vinyl sulfonamides, methacrylamides, and methyl acrylates, respectively) with aryl aldehydes via C(sp2)-H functionalization were reported. These reactions gave four different skeletal products respectively under environment-friendly and mild conditions. All these reactions are highly regioselective and effective, very suitable for the preparation of synthetic building blocks and compound library, the results will enrich current coupling chemistry of olefins with aldehydes and can be applied to other chemistry areas as well.

Copper-catalyzed oxidative cascade coupling of N-alkyl-N-phenylacrylamides with aryl aldehydes

An oxidative cascade coupling reaction was developed between N-alkyl-N-phenylacrylamides and aryl aldehydes using CuCl2/TBHP (tert-butyl hydroperoxide) as a catalyst and oxidant. The reaction involves oxidative cross coupling of the activated alkene Csp2-H from the N-alkyl-N-phenylacrylamide with the aldehyde Csp2-H bond (-CHO), followed by metal-mediated direct aryl Csp2-H functionalization/ cyclization to afford 3-(2-oxo-2-arylethyl)indolin-2-ones in good yields under mild reaction conditions without organic solvents involved.

Metal-free syntheses of oxindole derivatives via a benzoylation/substitution/desulfonylation/cyclization cascade

A benzoylation/substitution/desulfonylation/cyclization cascade reaction giving oxindole derivatives was discovered. The reaction used aromatic aldehydes and N-alkyl-N-(phenylsulfonyl)methacrylamides as starting materials, and proceeded under mild conditions without using toxic metal catalysts. 3-Methyl-3-aroyloxindole derivatives were formed in good yields.

Photocatalytic C-C Bond Activation of Oxime Ester for Acyl Radical Generation and Application

A unified strategy to generate acyl radical from oxime ester via selective C-C bond activation is reported. Under visible-light irradiation, single-electron transfer from fac-Ir(ppy)3 to related oxime takes place followed by a fast β-fragment of C-C bond to yield aryl and aliphatic acyl radicals, subsequently captured by diverse Michael acceptors. More interestingly, the single-electron transfer enables coupling with energy transfer of the excited fac-Ir(ppy)3 via enone intermediate formed in situ for cyclobutane formation.

Site-selective c-h acylation of pyridinium derivatives by photoredox catalysis

A strategy for visible-light-induced site-selective C-H acylation of pyridinium salts was developed by employing N-methoxy-or N-aminopyridinium salts, offering a powerful synthetic tool for accessing highly valuable C2- A nd C4-acylated pyridines. The met

Silver-Catalyzed Decarboxylative Radical Addition/Cyclization of α,α-Difluoroarylacetic Acids with Acrylamides To Synthesize Difluorinated Oxindoles

A facile silver-catalyzed decarboxylative radical addition/cyclization reaction of α,α-difluoroarylacetic acids and acrylamides has been disclosed. The method provides a highly attractive approach to synthesize a series of difluorinated oxindoles that contain various functional groups in moderate to good yields under mild conditions. Moreover, experimental studies reveal that the CF2 group of the α,α-difluoroarylacetic acids plays a vital role in the transformation.

Transition-Metal-Free TBAI-Facilitated Addition-Cyclization of N-Methyl-N-arylacrylamides with Arylaldehydes or Benzenesulfonohydrazides: Access to Carbonyl- and Sulfone-Containing N-Methyloxindoles

A highly efficient addition-cyclization of N-methyl-N-arylacrylamides with arylaldehydes or benzenesulfonohydrazides was developed using a catalytic amount of the quaternary ammonium salt (TBAI) under metal-free conditions, leading to the carbonyl- and sulfone-containing oxindoles. Compared to previous methods, which require excessive amounts of explosive organic peroxides and precious or toxic metal reagents, the present protocol, which gave access to 3,3-disubstituted oxindoles, is a safe and green approach, resulting in the formation of various useful carbonyl- and sulfone-containing oxindoles in yields of 40-94%.

Visible-Light-Mediated Photocatalytic Difunctionalization of Olefins by Radical Acylarylation and Tandem Acylation/Semipinacol Rearrangement

A novel method for the mild photoredox-mediated tandem radical acylarylation and tandem acylation/semipinacol rearrangement has been developed. The synthesis of highly functionalized ketones bearing all-carbon α- or β-quaternary centers has been achieved

Photocatalyst-free hypervalent iodine reagent catalyzed decarboxylative acylarylation of acrylamides with α-oxocarboxylic acids driven by visible-light irradiation

A hypervalent iodine(iii) reagent catalyzed carbonylarylation of acrylamides with α-oxocarboxylic acids driven by visible-light without a photoredox catalyst has been developed. The reactions generate the corresponding products in good yields at room temperature. Experiments indicate that a blue LED (450-455 nm) is the most effective energy for the cleavage of the oxygen-iodine bond to initiate the reaction. Mechanistic studies further demonstrate that the reaction undergoes a cascade decarboxylative radical addition/cyclization process along with releasing CO2 and H2.

Transition-Metal-Free Synthesis of Carbonyl-Containing Oxindoles from N-Arylacrylamides and α-Diketones via TBHP- or Oxone-Mediated Oxidative Cleavage of C(sp2)-C(sp2) Bonds

Carbonyl-containing oxindoles can be prepared from N-arylacrylamides and α-diketones by TBHP- or oxone (KHSO5)-mediated C(sp2)-C(sp2) bond cleavage and new C(sp2)-C(sp3) bond formation. This methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing inexpensive and readily available reagents, thus providing a practical and efficient approach to an important class of 3-(2-oxoethyl)indolin-2-ones which are highly valued synthetic intermediates of biologically active molecules. In this transformation, alkylcarbonyl-containing oxindoles were obtained in majority when N-arylacrylamides reacted with asymmetric aliphatic/aromatic α-diketones. On the basis of the preliminary experiments, a plausible mechanism of this transformation is disclosed.