75881-16-2Relevant articles and documents
Electrochemical Nonacidic N-Nitrosation/N-Nitration of Secondary Amines through a Biradical Coupling Reaction
Zhao, Ji-Ping,Ding, Lu-jia,Wang, Peng-Cheng,Liu, Ying,Huang, Min-Jun,Zhou, Xin-Li,Lu, Ming
, p. 5036 - 5043 (2020)
An acid-free N-nitrosation/nitration of the N?H bonds in secondary amines with Fe(NO3)3 ? 9H2O as the nitroso/nitro source through an electrocatalyzed radical coupling reaction was developed. Cyclic aliphatic amines and N-heteroaromatic compounds were N-nitrosated and N-nitrated, respectively, under mild conditions. Control and competition experiments, as well as kinetic studies, demonstrate that N-nitrosation and N-nitration involve two different radical reaction pathways involving N+ and N. radicals. Moreover, the electrocatalysis method enables the preferential activation of the N?H bond over the electrode and thus provides high selectivity for specific N atoms. Finally, this strategy exhibits a broad scope and provides a green and straightforward approach to generate useful N-nitroso/nitro compounds in good yields. (Figure presented.).
