69001-08-7Relevant articles and documents
Copper-Catalyzed Aerobic Oxidative Amidation of Benzyl Alcohols
Krabbe, Scott W.,Chan, Vincent S.,Franczyk, Thaddeus S.,Shekhar, Shashank,Napolitano, José G.,Presto, Carmina A.,Simanis, Justin A.
, p. 10688 - 10697 (2016)
A Cu-catalyzed synthesis of amides from alcohols and secondary amines using the oxygen in air as the terminal oxidant has been developed. The methodology is operationally simple requiring no high pressure equipment or handling of pure oxygen. The commercially available, nonprecious metal catalyst, Cu(phen)Cl2, in conjunction with di-tert-butyl hydrazine dicarboxylate and an inorganic base provides a variety of benzamides in moderate to excellent yields. The pKa of amine conjugate acid and electronics of alcohol were shown to impact the selection of base for optimal reactivity. A mechanism consistent with the observed reactivity trends, KIE, and Hammett study is proposed.
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.
