106914-36-7Relevant academic research and scientific papers
Electron-Catalyzed Aminocarbonylation: Synthesis of α,β-Unsaturated Amides from Alkenyl Iodides, CO, and Amines
Picard, Baptiste,Fukuyama, Takahide,Bando, Takanobu,Hyodo, Mamoru,Ryu, Ilhyong
supporting information, p. 9505 - 9509 (2021/12/09)
Aminocarbonylation of alkenyl iodides with CO and amines proceeded under heating to produce α,β-unsaturated amides in good yields (23 examples, 71% average yield). This catalyst-free method exhibited good functional-group tolerance, and open a straightforward access to functionalized acrylamides, as illustrated by the synthesis of Ilepcimide. A hybrid radical/ionic mechanism involving chain electron transfer is proposed for this transformation.
Catalytic hydrogenation of α,β-unsaturated carboxylic acid derivatives using copper(i)/N-heterocyclic carbene complexes
Zimmermann, Birte M.,Kobosil, Sarah C. K.,Teichert, Johannes F.
supporting information, p. 2293 - 2296 (2019/02/27)
A simple and air-stable copper(i)/N-heterocyclic carbene complex enables the catalytic hydrogenation of enoates and enamides, hitherto unreactive substrates employing homogeneous copper catalysis and H2 as a terminal reducing agent. This atom economic transformation replaces commonly employed hydrosilanes and can also be carried out in an asymmetric fashion.
Enantioselective epoxidation of β,β-disubstituted enamides with a manganese catalyst and aqueous hydrogen peroxide
Clarasó, Carlota,Vicens, Laia,Polo, Alfonso,Costas, Miquel
, p. 2430 - 2435 (2019/03/29)
Enantioselective epoxidation of β,β-disubstituted enamides with aqueous hydrogen peroxide and a novel manganese catalyst is described. Epoxidation is stereospecific and proceeds fast under mild conditions. Amides are disclosed as key functional groups to enable high enantioselectivity.
Palladium-Catalyzed Double-Carbonylation of Alkenyl Halides with Secondary Amines to Give α-Keto Amides
Son, Tae-il,Yanagihara, Hisayoshi,Ozawa, Fumiyuki,Yamamoto, Akio
, p. 1251 - 1258 (2007/10/02)
The double-carbonylation reaction of alkenyl halides with diethylamine in the presence of palladium catalysts has been examined in detail.The reaction gives α-keto amide together with amide, the single carbonylation by-product.The yield of α-keto amide is strongly dependent on the nature of alkenyl halide.Alkenyl bromides or iodides having phenyl group(s) as substituent(s) on the vinyl group are successfully double-carbonylated under appropriate reaction conditions and the corresponding α-keto amides are obtained in good to modest yields together with amides.In contrast, the reactions of alkenyl halides without a phenyl group give amides exclusively.In order to clarify the reason for the substrate-specificity in the reaction, series of alkenyl- and alkenoylpalladium(II) complexes, the presumed intermediates in the catalytic reactions, have been prepared and their reactions with secondary amines, carbon monoxide, and alkenyl halides were examined.The study suggests the operation of three types of processes for amide formation in the catalytic reactions.Possible mechanism for amide as well as α-keto amide formation are discussed.
