Microwave-Promoted Synthesis of 1-Tetralones via Iminyl Radical-Mediated 1,5-Hydrogen Atom Transfer
Microwave irradiation of <i>O</i>-phenyloximes produces 1-tetralones via N-O homolysis, 1,5-hydrogen atom transfer (HAT), and cyclization of a radical intermediate onto an aromatic ring. The HAT step is facilitated by coordination of Lewis acid InCl<sub>3</sub>·H<sub>2</sub>O to an iminyl radical. The reaction is rapid and exhibits a broad substrate scope. A larger scale transformation can be performed using conventional heating instead of microwave irradiation.
Authors
- Jatinder Singh (ORCID: https://orcid.org/0000-0002-2605-7107)
- Jesús Botello (ORCID: https://orcid.org/0000-0002-6255-2973)
- Steven L. Castle (ORCID: https://orcid.org/0000-0002-7837-4964)
- Gracie Damstedt
- Spencer A. Jones
- Osasere Jude-Kelly Osayawe (ORCID: https://orcid.org/0000-0002-6272-9097)
- Joshua S. Payne (ORCID: https://orcid.org/0000-0002-4372-9307)
- Elias D. Griffin (ORCID: https://orcid.org/0009-0005-2890-5201)
Institutions
- Brigham Young University (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-02-05
- DOI
- https://doi.org/10.1021/acs.joc.4c02887
- Citations
- 2
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Brigham Young University
- ACS Division of Organic Chemistry
- Division of Chemistry