64859-23-0

Upstream product

• 1749-19-5 phenyl(1-phenylethylidene)amine 
• 650-51-1 sodium trichloroacetate 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 62-53-3 aniline 
• 46114-86-7 pyruvanilide 
• 71-43-2 benzene 
• 50-00-0 formaldehyd 
• 621-06-7 2,N-diphenylacetamide 
• 39773-12-1 N-phenyl-2-bromo-acrylic acid amide 
• 98-80-6 phenylboronic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 492-38-6 2-phenylacrylic acid 
• 51246-20-9 1-phenyl-1-iodoethylene 

Downstream Products

• 231289-51-3 1-benzyl-3-phenylquinolin-2(1H)-one 
• 860755-99-3 3,N-diphenyl-succinamic acid methyl ester 
• 6017-78-3 (+/-)-1-phenyl-3-phenylpyrrolidine-2,5-dione 

Relevant academic research and scientific papers

Synthesis of Amides-Functionalized POPs-Supported Nano-Pd Catalysts for Phosphine Ligand-Free Heterogeneous Hydroaminocarbonylation of Alkynes

Development of an approach for synthesis of efficient heterogeneous catalyst toward carbonylation reaction remains a challenge. Herein, we report our results of design and precise synthesis of amide-functionalized porous organic polymers (POPs) supported nano-Pd, and its applying in the first example of heterogeneous palladium-catalyzed hydroaminocarbonylation of alkynes under phosphine ligand-free conditions. A wide range of terminal alkynes and amines with various functional groups are smoothly converted into the corresponding branched α, β-unsaturated amides in moderate to good yields with high regioselectivity. The good catalytic performance of amides-functionalized POPs supported nano-Pd catalyst should be attributed to fine regulation of the catalytically active sites of the heterogeneous catalyst at the molecular level. The present study provided meaningful insights to design heterogeneous catalysts for phosphine ligand-free carbonylation reaction. (Figure presented.).

Bromo Radical-Mediated Photoredox Aldehyde Decarbonylation towards Transition-Metal-Free Hydroalkylation of Acrylamides at Room Temperature

Herein, we report a visible-light-mediated hydroalkylation reaction of alkenes using easily available aldehydes as alkyl sources via bromo radical-promoted photoredox decarbonylation. This protocol provides an alternative entry to C(sp3)?C(sp3) bond formation and features considerable advantages including mild and clean reaction conditions, obviation for transition-metal catalyst, and good functional group compatibility.

Anionic Bisoxazoline Ligands Enable Copper-Catalyzed Asymmetric Radical Azidation of Acrylamides

Asymmetric radical azidation for the synthesis of chiral alkylazides remains a tremendous challenge in organic synthesis. We report here an unprecedented highly enantioselective radical azidation of acrylamides catalyzed by 1 mol % of a copper catalyst. The substrates were converted to the corresponding alkylazides in high yield with good-to-excellent enantioselectivity. Notably, employing an anionic cyano-bisoxazoline (CN-Box) ligand is crucial to generate a monomeric CuII azide species, rather than a dimeric CuII azide intermediate, for this highly enantioselective radical azidation.

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor

An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.

Systematic Study of the Glutathione Reactivity of N-Phenylacrylamides: 2. Effects of Acrylamide Substitution

A comprehensive understanding of structure-reactivity relationships is critical to the design and optimization of cysteine-targeted covalent inhibitors. Herein, we report glutathione (GSH) reaction rates for N-phenyl acrylamides with varied substitutions at the α- and β-positions of the acrylamide moiety. We find that the GSH reaction rates can generally be understood in terms of the electron donating or withdrawing ability of the substituent. When installed at the β-position, aminomethyl substituents with amine pKa's > 7 accelerate, while those with pKa's 7 slow the rate of GSH addition at pH 7.4, relative to a hydrogen substituent. Although a computational model was able to only approximately capture experimental reactivity trends, our calculations do not support a frequently invoked mechanism of concerted amine/thiol proton transfer and C-S bond formation and instead suggest that protonated aminomethyl functions as an electron-withdrawing group to reduce the barrier for thiolate addition to the acrylamide.

Direct Csp3-H methylenation of 2-arylacetamides using DMF/Me2NH-BH3 as the methylene source

A direct Csp3-H methylenation of 2-arylacetamides using DMF/Me2NH-BH3 as the methylene source was developed. The formyl group of DMF delivered the carbon and one hydrogen atoms, and the Me2NH-BH3 dona

Pd-catalyzed hydroaminocarbonylation of alkynes with aliphatic amines and its mechanism study

This work describes the hydroaminocarbonylation of alkynes with aliphatic amines without the addition of any acid additive. Excellent conversion and regioselectivity toward the formation of branched amides were obtained over a dppp-based Pd-catalytic syst

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.

High-valent palladium-promoted formal Wagner-Meerwein rearrangement

An oxy-palladation, formal Wagner-Meerwein rearrangement and fluorination cascade has been established for generating fluorinated oxazolidine-2,4-diones and oxazolidin-2-ones. The reaction has a broad substrate scope in which both aryl and alkyl groups can be utilized as efficient migrating groups. Experimental evidence suggests that the reaction is initiated by anti-oxy-palladation of the olefin, followed by oxidative generation of an alkyl PdIV intermediate and a concerted migration-fluorination.