41852-31-7Relevant academic research and scientific papers
Synthesis of α-aminonitriles using aliphatic nitriles, α-amino acids, and hexacyanoferrate as universally applicable non-toxic cyanide sources
Nauth, Alexander M.,Konrad, Tim,Papadopulu, Zaneta,Vierengel, Nina,Lipp, Benjamin,Opatz, Till
, p. 4217 - 4223 (2018/09/29)
In cyanation reactions, the cyanide source is often directly added to the reaction mixture, which restricts the choice of conditions. The spatial separation of cyanide release and consumption offers higher flexibility instead. Such a setting was used for the cyanation of iminium ions with a variety of different easy-to-handle HCN sources such as hexacyanoferrate, acetonitrile or α-amino acids. The latter substrates were first converted to their corresponding nitriles through oxidative decarboxylation. While glycine directly furnishes HCN in the oxidation step, the aliphatic nitriles derived from α-substituted amino acids can be further converted into the corresponding cyanohydrins in an oxidative C-H functionalization. Mn(OAc)2 was found to catalyze the efficient release of HCN from these cyanohydrins or from acetone cyanohydrin under acidic conditions and, in combination with the two previous transformations, permits the use of protein biomass as a non-toxic source of HCN.
Reactions Catalysed by a Binuclear Copper Complex: Relay Aerobic Oxidation of N-Aryl Tetrahydroisoquinolines to Dihydroisoquinolones with a Vitamin B1 Analogue
Liu, Yuxia,Wang, Chao,Xue, Dong,Xiao, Miao,Liu, Jiao,Li, Chaoqun,Xiao, Jianliang
supporting information, p. 3062 - 3066 (2017/03/13)
N-Aryl tetrahydroisoquinolines were oxidised to dihydroisoquinolones through the relay catalysis of a binuclear paddle-wheel copper complex and a vitamin B1 analogue with oxygen as oxidant. Mechanistic studies revealed that the copper catalyst oxidises amines to the corresponding iminium salts, which are then oxygenated to lactam products by catalysis of the vitamin B1 analogue.
Visible light-induced oxidative coupling reaction: Easy access to Mannich-type products
Zhao, Guolei,Yang, Chao,Guo, Lin,Sun, Hongnan,Chen, Chao,Xia, Wujiong
supporting information; experimental part, p. 2337 - 2339 (2012/04/18)
An efficient methodology for the functionalization of sp3 C-H bond adjacent to nitrogen has been developed utilizing visible light-induced photoredox catalysis. Through optimization of solvent and light source, the reaction can be rapidly achie
Mechanistic studies on a Cu-catalyzed aerobic oxidative coupling reaction with N-phenyl tetrahydroisoquinoline: Structure of intermediates and the role of methanol as a solvent
Boess, Esther,Sureshkumar, Devarajulu,Sud, Abhishek,Wirtz, Cornelia,Fares, Christophe,Klussmann, Martin
supporting information; experimental part, p. 8106 - 8109 (2011/07/08)
The mechanism of an aerobic copper-catalyzed oxidative coupling reaction with N-phenyl tetrahydroisoquinoline was investigated. The oxidized species formed from the reaction of the amine with the copper catalyst were analyzed by NMR-spectroscopy. An iminium dichlorocuprate was found to be the reactive intermediate and could be structurally characterized by X-ray crystallography. The effect of methanol to effectively stabilize the iminium ion was investigated and shown to be beneficial in an oxidative allylation reaction.
