7464-44-0Relevant articles and documents
Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis
K?ring, Laura,Sitte, Nikolai A.,Bursch, Markus,Grimme, Stefan,Paradies, Jan
supporting information, p. 14179 - 14183 (2021/09/03)
The metal-free catalytic hydrogenation of secondary carboxylic acid amides is developed. The reduction is realized by two new catalytic reactions. First, the amide is converted into the imidoyl chloride by triphosgene (CO(OCCl3)2) using novel phosphorus(V) catalysts. Second, the in situ generated imidoyl chlorides are hydrogenated in high yields by an FLP-catalyst. Mechanistic and quantum mechanical calculations support an autoinduced catalytic cycle for the hydrogenation with chloride acting as unusual Lewis base for FLP-mediated H2-activation.
Tert -Butyl nitrite promoted transamidation of secondary amides under metal and catalyst free conditions
Sureshbabu, Popuri,Azeez, Sadaf,Chaudhary, Priyanka,Kandasamy, Jeyakumar
, p. 845 - 850 (2019/01/30)
A mild and efficient method is demonstrated for the transamidation of secondary amides with various amines including primary, secondary, cyclic and acyclic amines in the presence of tert-butyl nitrite. The reaction proceeds through the N-nitrosamide intermediate and provides the transamidation products in good to excellent yields at room temperature. Moreover, the developed methodology does not require any catalyst or additives.
Tf2O-Mediated Intermolecular Coupling of Secondary Amides with Enamines or Ketones: A Versatile and Direct Access to β-Enaminones
Liu, Yong-Peng,Zhu, Cheng-Jie,Yu, Cun-Cun,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 7169 - 7174 (2019/11/16)
Based on the Tf2O-mediated intermolecular reaction of secondary amides with enamines derived from ketones, a novel approach to β-enaminones has been developed. The reaction is widely functional group tolerant and highly chemoselective. In the presence of 4 ? molecular sieves, the method can be extended to the one-pot condensation of secondary amides with ketones for NH β-enaminones synthesis.