Copper-catalyzed direct oxidative synthesis of α-ketoamides from aryl methyl ketones, amines, and molecular oxygen

Oxidative cross-dehydrogenative coupling of amines and α-carbonyl aldehydes over heterogeneous Cu-MOF-74 catalyst: A ligand- and base-free approach

“…The necessity of oxidant in reaction progress was confirmed by the low yield obtained from reactions conducted in inert atmosphere (entry 14). In comparison, similar reported reactions under homogeneous copper catalysis employed 10 -20 % catalysts and toluene solvent and atmospheric oxygen were showed to be optimal [4,11,12]. …”

“…Jiao and co-workers subsequently changed the synthetic strategy to the CuBr-catalyzed aerobic oxidative coupling of aryl acetaldehydes with anilines [1]. Ji and Du also reported the CuI-catalyzed direct oxidative transformation to form -ketoamides from aryl methyl ketones, amines, and molecular oxygen via a one-pot tandem process [4]. To overcome the existing drawbacks, Jiao and co-workers performed the CuBr-catalyzed aerobic oxidative cross-dehydrogenative coupling of amines with -carbonyl aldehydes in the presence of 2,2'-bipyridine ligand and pyridine base [12].…”

“…They were frequently used as versatile and important intermediates in numerous functional group transformations [1][2][3][4]. Conventionally, these structures were achieved by several synthetic strategies, including the condensation of -keto acids with amines [5], the oxidative coupling of aliphatic aldehydes with isocyanides [6], the oxidation of -hydroxyamides and -aminoamides [7], the double carbonylative amination of aryl halides [8,9], and the reaction of carbamoylstannane and carbamoysilane with acid chlorides [10].…”

Aerobic Copper-Catalyzed Organic Reactions

“…606 Both electron-rich and electron-poor substitution on the aryl ring is tolerated, though yields are higher in electron-poor aryls. Aryls with ortho -substitution are also successful.…”

Palladium Catalyzed Oxidation of Ynamides Using Dimethyl Sulfoxide as Oxidant: A Facile Way to Synthesizeα-Ketoamide Derivatives

“…此类化合物的传统的合成方法 是 α-酮酸的酰胺化反应 [10] . 通过芳基甲基酮 [11] 、芳基乙 炔 [12] 、芳基乙烯 [13] 、芳基乙烷 [14] 、α-羰基醛 [15] 、芳基乙 醛 [16] 的氧化酰胺化也是一类常用的方法. 另外芳基 碘 [17] 或吲哚 [18] 的双羰化酰胺化也可构建 α-酮酰胺衍生 物.…”