3672-66-0

Upstream product

• 6077-10-7 bis(phenylethynyl)mercury 
• 122-04-3 4-nitro-benzoyl chloride 
• 32584-71-7 diphenyl(phenylethynyl)stibine 
• 636-98-6 p-nitrobenzene iodide 
• 201230-82-2 carbon monoxide 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 555-16-8 4-nitrobenzaldehdye 
• 536-74-3 phenylacetylene 
• 586-78-7 para-nitrophenyl bromide 
• 6738-06-3 phenylethynylmagnesium bromide 
• 64-18-6 formic acid 
• 21890-32-4 tetrakis(phenylethynyl)tin 
• 67-66-3 chloroform 
• 3757-88-8 tributylstannylethynylbenzene 

Downstream Products

• 858837-01-1 6-(4-nitro-phenyl)-2-oxo-4-phenyl-2H-pyran-3-carboxylic acid ethyl ester 
• 39833-49-3 1-phenyl-3-(4-nitrophenyl)-2-propyn-1-one 
• 131293-13-5 3-N,N-diethylamino-1-p-nitrophenyl-3-phenyl-2-propen-1-one 
• 63500-30-1 1-methyl-3-phenyl-5-(4-nitrophenyl)pyrazole 
• 63500-31-2 1-methyl-3-(4-nitrophenyl)-5-phenyl-1H-pyrazole 
• 1245504-79-3 (2-(4-fluoro-2-nitrophenyl)-5-phenyl-2H-1,2,3-triazol-4-yl)(4-nitrophenyl)methanone 
• 1245504-80-6 (2-(2-chlorobenzyl)-5-phenyl-2H-1,2,3-triazol-4-yl)(4-nitrophenyl)methanone 
• 1315379-24-8 dimethyl 5-nitro-1-oxo-3-phenyl-1H-inden-2-ylphosphonate 
• 1337529-26-6 2-(diphenylmethylene)-3-hydroxy-1,3-bis(4-nitrophenyl)-5-phenylpent-4-yn-1-one 
• 85658-02-2 4-(4-nitrophenyl)-2-phenylfuran 

Relevant academic research and scientific papers

Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones

An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is

Selective Thiocyanation and Aromatic Amination to Achieve Organized Annulation of Enaminone with Thiocyanate

A tandem insertion of thiocyanate to enamine was performed for the regioselective synthesis of multisubstituted benzoimidazo[2,1-b]thiazoles. This method was shown to be effective in addressing the issue of isomerization encountered in common strategies. With a change made to the leading group on the aniline fragment of enamine, the reaction achieved different transformations, thus enabling multisubstituted benzo[4,5]imidazo[2,1-b]thiazoles and thiazoles in satisfactory yields.

Enantioselective [3 + 2] annulation of 4-isothiocyanato pyrazolones and alkynyl ketones under organocatalysis

An asymmetric [3 + 2] annulation reaction of 4-isothiocyanato pyrazolones with alkynyl ketones in the presence of an organic catalyst derived from a cinchona alkaloid under mild conditions is realized. This protocol provides unprecedented expeditious access to a wide range of optically active spiro[pyrroline-pyrazolones] with various electronic properties in high yields with good to excellent enantioselectivities.

Reduced graphene oxide supported copper oxide nanocomposites: An efficient heterogeneous and reusable catalyst for the synthesis of ynones, 1,3-diynes and 1,5-benzodiazepines in one-pot under sustainable reaction conditions

A greener and efficient method for the synthesis of ynones and 1,3-diynes using copper oxide nanoparticles (CuONPs) doped reduced graphene oxide (CuO@rGO) catalyst under palladium, ligand and solvent free conditions have been developed. The catalyst was s

Palladium(II) on 4 ? Molecular Sieves: A Simple and Reusable Catalyst for the Preparation of Ynones

Abstract: Pd2+ on 4?? molecular sieves support has been prepared and investigated. The catalyst has successfully been used in the reaction of acyl chlorides and terminal alkynes yielding ynones. The catalyst can be reused without significant lo

N-Heterocyclic Carbene-Catalyzed Synthesis of Ynones via C-H Alkynylation of Aldehydes with Alkynyliodonium Salts - Evidence for Alkynyl Transfer via Direct Substitution at Acetylenic Carbon

Alkynylation of aldehydes with alkynyl(aryl)iodonium salts catalyzed by an N-heterocyclic carbene (NHC) has been developed. The application of the organocatalyst and the hypervalent iodine group transfer reagent allowed for metal-free C-H functionalization and C-C bond formation. The reaction proceeds under mild conditions, at -40 °C and in the presence of an amine base, providing access to an array of heteroaryl-propargyl ketones containing various substituents in good to excellent yields. The mechanism of the reaction was investigated by means of both experiments and density functional theory calculations. 13C-labeling and computations determined that the key alkynyl transfer step occurs via an unusual direct substitution at an acetylenic carbon, wherein an iodine-based leaving group is exchanged by a Breslow intermediate nucleophile. Moreover, kinetic studies revealed that the turnover-limiting step of the catalytic cycle is the generation of the Breslow intermediate, whereas the subsequent C-C bond formation is a fast process. These results are fully reproduced and rationalized by the calculated full free energy profile of the reaction, showing that the largest energy span is located between the protonated form of NHC catalyst and the transition state for the carbene attack on the aldehyde substrate.

Palladium-catalyzed carbonylative Sonogashira cross-coupling for the synthesis of alkynones with formic acid as the CO source

Abstract: A practical and efficient palladium-catalyzed carbonylative Sonogashira cross-coupling reaction for the synthesis of alkynones from aryl iodides, alkynes, and formic acid as the CO source has been described. Under the assistance of PPh3/I2, formic acid can be used as the CO source for synthesis of alkynones in moderate–good yields. Furthermore, it is also successfully applied for the modification of natural products, such as vindoline and tabersonin, to obtain the corresponding products.

Fast and Efficient Continuous Flow Method for the Synthesis of Ynones and Pyrazoles

In this study, we developed a convenient and efficient two-step method for the synthesis of ynones in a flow reactor, through the generation of lithium acetylide and its subsequent reactions with acid chlorides. Using this approach, we obtained the ynones in moderate to good yields at room temperature. Moreover, we transformed the ynones into pyrazole derivatives through coupling with hydrazines. This transition metal-free process, mild reaction conditions, and broad functional group tolerance are all attractive features in comparison with conventional bench-top methods.

Synthesis of 4,5-disubstituted-1H-1,2,3-triazoles

Abstract: Two-step procedure, a palladium catalyzed Sonogashira cross-coupling reaction of aroyl chlorides with aryl acetylenes, and 1,3-dipolar cycloaddition of the 1,3-diarylprop-2-yn-1-ones with sodium azide under catalyst free conditions achieved the

Nickel catalysed carbonylative Sonogashira reaction for the synthesis of diarylalkynones and 2-substituted flavones

The nickel catalyzed, palladium/phosphine free carbonylative Sonogashira reaction of terminal alkynes with substituted aryl and heteroaryl iodides is described. This protocol provides mild and robust conditions to synthesize a variety of substituted aryl α,β-alkynyl ketones and flavones in good to excellent isolated yields. This methodology tolerates several functional groups such as electron donating (methyl, isopropyl, tert-butyl, methoxy) as well as electron withdrawing (trifluoromethyl, nitro, esters, nitrile) groups on the terminal alkynes and iodides.