85274-97-1

Upstream product

• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 
• 25725-56-8 4'-methoxy-deoxybenzoin-seqtrans-oxime 
• 201230-82-2 carbon monoxide 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 62-53-3 aniline 
• 156-38-7 4-hydroxyphenylacetate 
• 131179-71-0 4-<(anilinocarbonyl)methyl>phenol 
• 74-88-4 methyl iodide 
• 768-60-5 4-methoxyphenylacetylen 
• 3422-01-3 tert-butyl phenylcarbamate 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 
• 123-11-5 4-methoxy-benzaldehyde 
• 66003-76-7 Diphenyliodonium triflate 

Downstream Products

• 85274-80-2 2-chloro-3-(4-methoxyphenyl)quinoline 
• 51009-26-8 N-(2-(4-Methoxyphenyl)ethyl)aniline 
• 96719-07-2 N-[2-(4-Methoxy-phenyl)-ethyl]-N-phenyl-benzamide 
• 110487-17-7 {2-[3-(4-Methoxy-phenyl)-quinolin-2-ylsulfanyl]-ethyl}-dimethyl-amine 

Relevant academic research and scientific papers

A Concise Total Synthesis of Dictyodendrins F, H, and i Using Aryl Ynol Ethers as Key Building Blocks

We report a concise total synthesis of dictyodendrin F and the first total syntheses of dictyodendrins H and I in six steps. In these syntheses, aryl ynol ethers were employed as the key building blocks to introduce aryl and heteroaryl rings in the dictyodendrins. This rapid synthesis utilized a novel hetero-[2 + 2]-cycloaddition reaction between two aryl ynol ethers to yield a cyclobutenone ring. The cyclobutenone was sequentially converted into a highly substituted carbazole via a retro-4π/6π-electrocyclization-N-acylation cascade reaction to provide the dictyodendrin core. Consecutive intramolecular oxidative coupling and deprotection gave dictyodendrins F, H, and I.

Copper-catalyzed transformation of alkyl nitriles to N -arylacetamide using diaryliodonium salts

This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.

Solvent- and transition metal-free amide synthesis from phenyl esters and aryl amines

A general, economical, and environmentally friendly method of amide synthesis from phenyl esters and aryl amines was developed. This new method has significant advantages compared to previously reported palladium-catalyzed approaches. The reaction is performed transition metal- and solvent-free, using a cheap and environmentally benign base, NaH. This approach enabled us to obtain target amides in high yields with high atom economy.

Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides

Complex CpRuCl(PPh3)2 catalyzes reactions of terminal alkynes with 4-picoline N-oxide and primary and secondary amines to afford the corresponding amides. The reactions occur in chlorinated solvent and aqueous medium, showing applications in peptide chemistry. Stoichiometric studies reveal that the true catalysts of the processes are the vinylidene cations [CpRu(=C=CHR)(PPh3)2]+ which are oxidized to the Ru(η2-CO)-ketenes by the N-oxide. Finally, nucleophilic additions of primary and secondary amines to the free ketenes yield the corresponding amides.

[Co(MeTAA)] Metalloradical Catalytic Route to Ketenes via Carbonylation of Carbene Radicals

An efficient synthetic strategy towards beta-lactams, amides, and esters involving “in situ” generation of ketenes and subsequent trapping with nucleophiles is presented. Carbonylation of carbene radical intermediates using the cheap and highly active cobalt(II) tetramethyltetraaza[14]annulene catalyst [Co(MeTAA)] provides a convenient one-pot synthetic protocol towards substituted ketenes. N-tosylhydrazones are used as carbene precursors, thereby bridging the gap between aldehydes and ketenes. Activation of these carbene precursors by the metalloradical cobalt(II) catalyst affords CoIII-carbene radicals, which subsequently react with carbon monoxide to form ketenes. In the presence of a nucleophile (imine, alcohol, or amine) in the reaction medium the ketene is immediately trapped, resulting in the desired products in a one-pot synthetic protocol. The β-lactams formed upon reaction with imines are produced in a highly trans-selective manner.

Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation

An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.

Methods for preparing amide compounds using alkynes and methods for preparing peptides using the same

The present invention relates to a method for preparing an amide compound, which comprises a step of agitating an alkyne and an N-hydroxy compound in an organic solvent in the presence of a transition metal catalyst to form an amide bond, and a method for preparing a peptide using the same. According to the present invention, the amidation reaction does not depend on polar reactivity, such as the conventional simple nucleophilicity and electrophilicity, but is based on a reaction derived from coordination reactivity between an alkyne and a transition metal, and thus shows excellent chemical selectivity. In addition, the method does not require a consumptive step such as attachment and detachment of a protecting group but includes a simple process during the synthesis of a peptide. Thus, the method is very effective for preparing a polypeptide compound. The method also has 100% of atomic economic efficiency since the starting materials are not lost during the reaction.COPYRIGHT KIPO 2017

Novel green acylamide synthesis method through quaternary ammonium salt C-N bond fracture

The invention provides a novel green acylamide synthesis method through quaternary ammonium salt C-N bond fracture. The structure of the compound is expressed by methods such as H NMR, C, NMR and HRMS and is confirmed. A series of phenmethyl quaternary ammonium salts and aminated compounds are used; under the catalysis effect of PdCl2(dppf), PPh3 is used as a ligand, Na2CO3 is used as the alkali, and corresponding amide compounds are generated in the 100-DEG C CO atmosphere in a pHMe/DMSO mixed solvent. The method has the advantages that the efficiency is high; the toxicity is low; the conditions are mild; the application range of the substrate is wide; the yield is high; the product purity is high; the separation is convenient; the method can be applicable to large-scale preparation; the application prospects are wide.

Modular Synthesis of Arylacetic Acid Esters, Thioesters, and Amides from Aryl Ethers via Rh(II)-Catalyzed Diazo Arylation

One-pot formation of arylacetic acid esters, thioesters, and amides via Rh(II)-catalyzed arylation of a Meldrum's acid-derived diazo reagent with electron-rich arenes is described. The methodology was used to efficiently synthesize an anticancer compound.

Metal-free hydration of ynamides: Convenient approach to amides

The trifluoroacetic acid (TFA) mediated hydration of ynamides was developed, which is an efficient approach for the synthesis of N-monosubstituted amides. This convenient method is effective with a wide range of substrates under room temperature condition, and the products are obtained in high to excellent yields through an easy work-up process.