The Azobis(isobutyronitrile)-Promoted Oxidative Radical α-Cyanation of Imine under Atmospheric O<sub>2</sub>
Herein, we report an azobis(isobutyronitrile) (AIBN)-promoted radical α-cyanation of <i>in situ</i> formed imine under atmospheric O<sub>2</sub>. This oxidative radical addition (ORA) procedure proceeds with the sequential homocleavage of AIBN, extrusion of N<sub>2</sub>, and capture of O<sub>2</sub> toward an O-centered radical, which is converted to a cyano radical by β-scission. Then, the insertion of the cyano radical into the imine C═N bond forms an aminyl radical, leading to α-cyano imine after 1,2-hydrogen atom transfer (HAT) and H abstraction. Such a transition-metal-free procedure features mild reaction conditions and a broad substrate scope, employing molecular O<sub>2</sub> as a clean terminal oxidant.
Authors
- Kui Zheng
- Zhenlian Wang
- Hailong Chen
- Jiang Cheng (ORCID: https://orcid.org/0000-0003-2580-1616)
- Yang Zhao (ORCID: https://orcid.org/0000-0002-7358-2027)
Institutions
- Wenzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-17
- DOI
- https://doi.org/10.1021/acs.orglett.4c03528
- Citations
- 2
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Wenzhou University