In Situ Generation of N-Unsubstituted Imines from Alkyl Azides and Their Applications for Imine Transfer via Copper Catalysis

Xuebin Liao describes the in situ generation of N-unsubstituted imines and their applications in Cu-catalyzed imine transfer.

N-Unsubstituted aliphatic imines have rarely been used in synthetic organic chemistry since this chemistry is affected by several drawbacks, especially the necessity of pre-forming protected imines and subsequently removing the N-protecting group.

To solve this problem, the group of Professor Xuebin Liao at Tsinghua University (Beijing, P. R. of China) developed a method to produce in situ N–H imines generated from alkyl azides. In addition, they also explored the reactivity of aliphatic N–H imines and their application in the unusual construction of multi-substituted pyridines or indole derivatives. The group developed a method to produce N–H imines in situ using an earth-abundant copper catalyst. Using this approach, they were able to successfully construct multi-substituted pyridines and indoles.


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