62258-29-1Relevant 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
Dubovtsev, Alexey Yu.,Shcherbakov, Nikolay V.,Dar'in, Dmitry V.,Kukushkin, Vadim Yu.
, p. 745 - 757 (2020/02/04)
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.
A general approach to selective functionalization of 1,2,4-triazines using organometallics in palladium-catalyzed cross-coupling and addition reactions
Alphonse, France-Aimee,Suzenet, Franck,Keromnes, Anne,Lebret, Bruno,Guillaumet, Gerald
, p. 2893 - 2899 (2007/10/03)
A selective way to obtain disubstituted 1,2,4-triazines in good yields by combining addition reactions and palladium-catalyzed cross-coupling reactions of organometallics with 3-methylsulfanyl-1,2,4-triazine is described.
Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether
Alphonse, France-Aimee,Suzenet, Franck,Keromnes, Anne,Lebret, Bruno,Guillaumet, Gerald
, p. 803 - 805 (2007/10/03)
(Matrix presented) Palladium-catalyzed cross-coupling of vinyl- and arylstannanes with π-electron-deficient heteroaromatics was performed in good yields. This Stille-type reaction was carried out with a methylthioether function as an electrophile in the presence of a copper(I) bromide-dimethyl sulfide complex.
Palladium-catalyzed 3-thiomethyltriazine-boronic acid cross coupling: Easy access to 3-substituted-1,2,4-triazines
Alphonse, France-Aimée,Suzenet, Franck,Keromnes, Anne,Lebret, Bruno,Guillaumet, Gérald
, p. 447 - 450 (2007/10/03)
The palladium-catalyzed coupling reaction of 3-thiomethyl-1, 2,4-triazine 1 with different organoboron compounds in the presence of copper(I) 3-methylsalicylate proceeds to afford the corresponding 3-substituted-1,2,4-triazines in good yield. This approach leads very easily to a large range of C-5 and C-6 unsubstituted as-triazines.
