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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*

*Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, People’s Republic of China, Email:

F. Huang, S. Zhang, Org. Lett., 2019, 21, 7430-7434.

DOI: 10.1021/acs.orglett.9b02740

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A reductive cleavage of the N-O bond in oxime ether promoted by SmI2 generates N-centered radicals, that undergo intramolecular cyclization to afford five-membered cyclic imines either via N-centered radical addition or N-centered anion nucleophilic substitution.

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Key Words

1-pyrrolines, samarium diiodide

ID: J54-Y2019