Iminyl Radicals by Reductive Cleavage of N−O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines

Fei Huang and Songlin Zhang^*（张松林）

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, People’s Republic of China

Org. Lett. 2019, 21, 7430--7434

A new generation method of N-centered radicals from the reductive cleavage of the N−O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic

substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.

链接：https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.9b02740