7332-96-9Relevant articles and documents
Copper/Iodine-Cocatalyzed C-C Cleavage of 1,3-Dicarbonyl Compounds Toward 1,2-Dicarbonyl Compounds
Chen, Li-Sha,Zhang, Lu-Bing,Tian, Yue,Li, Jin-Heng,Liu, Yong-Quan
supporting information, p. 5523 - 5526 (2020/09/02)
A new, general oxidative route to transformations of 1,3-dicarbonyl compounds to 1,2-dicarbonyl compounds by merging copper and I2 catalysis is described. This method is applicable to broad 1,3-dicarbonyl compounds, including 1,3-diketones, 1,3-keto esters and 1,3-keto amides. Mechanistical studies show that the reaction is achieved via the C–C bond cleavage and CO release cascades.
Palladium-Catalyzed Oxidative C≡C Triple Bond Cleavage of 2-Alkynyl Carbonyl Compounds Toward 1,2-Dicarbonyl Compounds?
Hu, Ming,Li, Jin-Heng,Luo, Mu-Jia,Zhou, Ming-Bo
, p. 553 - 558 (2020/04/20)
A new, general palladium-catalyzed oxidative strategy for the cleavage of the C≡C triple bond is presented. By employing PdCl2, CuBr2, TEMPO and air as the catalytic system and H2O as the carbonyl oxygen atom source, a wide range of 2-alkynyl carbonyl compounds, including 1,3-disubstituted prop-2-yn-1-ones, propiolamides and propiolates, lost an alkynyl carbon to access various 1,2-dicarbonyl compounds, e.g., 1,2-diones, 2-keto amides and 2-keto esters, through Wacker oxidation, intramolecular cyclization and C—C bond cleavage cascades.
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.