Visible light-mediated syntheses of unsymmetrical methylene-bridged bis-heterocycles via an alkoxy radical relay reaction

Ting Ting Yuan, Jing Chen, Le Nhan Pham, Sayan Paul, Lorenzo V. White, Jialong Li, Ping Lan, Michelle L. Coote, Martin G. Banwell, Yu Tao He

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

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 languageEnglish
Pages (from-to)4649-4657
Number of pages9
JournalOrganic Chemistry Frontiers
Volume10
Issue number18
Early online date7 Aug 2023
DOIs
Publication statusPublished - 21 Sept 2023

Keywords

  • Synthesis
  • bis-heterocycles

Fingerprint

Dive into the research topics of 'Visible light-mediated syntheses of unsymmetrical methylene-bridged bis-heterocycles via an alkoxy radical relay reaction'. Together they form a unique fingerprint.

Cite this