1268824-73-2

Upstream product

• 888329-88-2 3-(2-phenylethynyl)oxazolidin-2-one 
• 536-74-3 phenylacetylene 
• 5296-64-0 allyl phenyl thioether 
• 100-39-0 benzyl bromide 
• 104-81-4 4-Methylbenzyl bromide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 82323-46-4 phenylglyoxylic acid chloride p-toluenesulfonylhydrazone 
• 694-59-7 pyridine N-oxide 
• 931-19-1 2-methylpyridine N-oxide 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 

Relevant academic research and scientific papers

Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.

ortho-Alkylation of Pyridine N-Oxides with Alkynes by Photocatalysis: Pyridine N-Oxide as a Redox Auxiliary

A photocatalyzed ortho-alkylation of pyridine N-oxide with ynamides and arylacetylenes has been developed, which yields a series of α-(2-pyridinyl) benzyl amides/ketones. Mechanistic studies, including electrochemical studies, radical-trapping experiments, and Stern–Volmer fluorescence quenching studies demonstrate that pyridine N-oxide serves as both a redox auxiliary and radical acceptor to achieve the mild photocatalytic single-electron oxidation of carbon–carbon triple bonds with the generation of a cationic vinyl radical intermediate.

Palladium-Catalyzed Oxygenative Cross-Coupling of Ynamides and Benzyl Bromides by Carbene Migratory Insertion

A palladium-catalyzed oxygenative cross-coupling of ynamides and benzyl bromides has been developed. After subsequent hydrogenation, α,α-disubstituted amide derivatives were obtained in good yields. Migratory insertion of α-oxo palladium carbene species, generated by intermolecular oxidation, is proposed as the key step in this reaction. The study demonstrates the potential of ynamides to serve as carbene precursors in palladium-catalyzed C?C bond-forming cross-coupling reactions.

A 1, 2 - dione derivatives of synthetic method (by machine translation)

The invention discloses a synthesis method of 1, 2-dione derivatives by utilizing polyacetylenes. According to the method, in a nitrogen environment, polyacetylenes, an oxidant and an organic solvent are mixed up under the presence of zinc salt as a catalyst, and then heated to react with one another to obtain1, 2-dione derivatives. The substrate of the method is wide in compatibility, mild in condition and high in synthesis yield. The metal zinc salt adopted as the catalyst is low in price and environmentally-friendly. Easily available polyacetylenes are adopted as the substrate of the method, so that the method has the advantages of low cost, high yield, simple operation, readily available raw materials and easy industrial production.

Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds

Metal-free oxidation of ynamides is described, employing pyridine-N-oxides as oxidants under molecular iodine catalysis. In stark contrast to Br?nsted acid catalysis, iodophilic activation of ynamides diverts the reaction manifold into a dioxygenation pathway. This oxidation is very rapid at room temperature with only 2.5 mol % I2. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to deliver various benzil derivatives.

Synthesis of α-keto imides through copper-catalyzed oxidation of: N -sulfonyl ynamides

A novel copper-catalyzed N-oxide oxidation of N-sulfonyl ynamides is disclosed. This non-noble metal-catalyzed protocol enables facile and efficient access to valuable α-keto imides in generally good to excellent yields. Other notable features of this method include widespread availability of the substrates, compatibility with broad functional groups, a simple procedure, mild conditions, and in particular, no need to exclude moisture or air ("open flask").

A gold-catalysed fully intermolecular oxidation and sulfur-ylide formation sequence on ynamides

An efficient C-O, C-S and C-C bond-forming sequence leads to functionalised compounds bearing sulfur-substituted quaternary carbons. Ynamides are employed as diazo-equivalents to access the [2,3]-sigmatropic rearrangements of allyl sulfonium ylides by a t

Iodine-mediated oxidation of ynamides: A facile access to N-monosubstituted α-ketoamides and α-ketoimides

An efficient iodine-mediated oxidation reaction for ynamides has been developed to produce N-monosubstituted α-ketoamides and α-ketoimides. This oxidative method, which exhibits good functional group tolerance, was performed under mild conditions without a metal catalyst.

A combination of copper(0) powder and selectfluor enables generation of cationic copper species for mild 1,2-dicarbonylation of alkynes

A combination of copper powder and Selectfluor permits the generation of cationic copper species that efficiently catalyze 1,2-dicarbonylation of alkynes under mild conditions with water and dioxygen as inexpensive and environmentally benign sources of oxygen. Georg Thieme Verlag Stuttgart New York.

Gold-catalyzed synthesis of benzil derivatives and α-keto imides via oxidation of alkynes

An efficient process based on the gold-catalyzed redox reaction has been developed to oxidize 1,2-diarylacetylene or ynamide to 1,2-diaryldiketone or α-keto imide respectively. This process can tolerate a variety of functional groups and affords 1,2-dicarbonyl compounds in excellent yields under mild reaction conditions.