Abstract
Efficient and versatile syntheses of methylene-bridged bis-heterocycles that embody dihydroisoxazoline/pyridine or dihydroisoxazoline/quinoline pairings are described. These proceed under mild conditions and involve a visible light-mediated radical-relay sequence that begins with the homolysis of O-H bonds contained within β,γ-unsaturated oximes to generate oxygen-centred radicals that add to the tethered olefin. The ensuing carbon-centered radical is then trapped by an added N-heteroarenium salt. The results suggest that the radical-chain is sustained by hydrogen atom transfer between in situ generated methoxy radicals and oxime O-H bonds. Such outcomes provide new insights into alkoxy radical-mediated transformations promoted by visible light as well as access to new molecular scaffolds likely to be useful in a variety of settings.
Original language | English |
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Pages (from-to) | 4649-4657 |
Number of pages | 9 |
Journal | Organic Chemistry Frontiers |
Volume | 10 |
Issue number | 18 |
Early online date | 7 Aug 2023 |
DOIs | |
Publication status | Published - 21 Sept 2023 |
Keywords
- Synthesis
- bis-heterocycles