Microwave-PromotedSynthesis of 1‑Tetralonesvia 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.

Publication Details

Journal
Figshare
Published
2025-02-05
DOI
https://doi.org/10.1021/acs.joc.4c02887.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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Microwave-PromotedSynthesis of 1‑Tetralonesvia Iminyl Radical-Mediated 1,5-Hydrogen Atom Transfer

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Microwave-PromotedSynthesis of 1‑Tetralonesvia Iminyl Radical-Mediated 1,5-Hydrogen Atom Transfer

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Abstract

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.

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Mycorrhizal Fungi and Plant Interactions
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Microwave-PromotedSynthesis of 1‑Tetralonesvia Iminyl Radical-Mediated 1,5-Hydrogen Atom Transfer · Figshare (2025) | TGRS Research Map | TGRS