21384-41-8Relevant articles and documents
Ruthenium-catalyzed oxidative decyanative cross-coupling of acetonitriles with amines in air: A general access to primary to tertiary amides under mild conditions
Wang, Yuguang,Wu, Zhongli,Li, Qin,Zhu, Bingchun,Yu, Lei
, p. 3747 - 3757 (2017/09/07)
Catalyzed by Ru and in the presence of air and nucleophiles such as amines or ammonia, activation of the C-CN bond could be easily achieved under mild conditions to produce primary to tertiary amides in good to excellent yields. The use of accessible and functional-group-tolerant starting materials, a cheap, low-loading and recyclable catalyst, ligand-free conditions and excellent product yields are the advantages of the method. Moreover, compared with the Ritter reaction and hydration methods, this novel reaction has more comprehensive application scope.
Palladium-catalyzed Suzuki-Miyaura coupling of amides by carbon-nitrogen cleavage: General strategy for amide N-C bond activation
Meng, Guangrong,Szostak, Michal
supporting information, p. 5690 - 5707 (2016/07/06)
The first palladium-catalyzed Suzuki-Miyaura cross-coupling of amides with boronic acids for the synthesis of ketones by sterically-controlled N-C bond activation is reported. The transformation is characterized by operational simplicity using bench-stable, commercial reagents and catalysts, and a broad substrate scope, including substrates with electron-donating and withdrawing groups on both coupling partners, steric-hindrance, heterocycles, halides, esters and ketones. The scope and limitations are presented in the synthesis of >60 functionalized ketones. Mechanistic studies provide insight into the catalytic cycle of the cross-coupling, including the first experimental evidence for Pd insertion into the amide N-C bond. The synthetic utility is showcased by a gram-scale cross-coupling and cross-coupling at room temperature. Most importantly, this process provides a blueprint for the development of a plethora of metal catalyzed reactions of typically inert amide bonds via acyl-metal intermediates. A unified strategy for amide bond activation to enable metal insertion into N-C amide bond is outlined (Scheme 1).
Phosphine-catalyzed heine reaction
Martin, Allen,Casto, Kathleen,Morris, William,Morgan, Jeremy B.
supporting information; experimental part, p. 5444 - 5447 (2011/12/05)
Aziridines are important synthetic intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions o
