Synthesis of 2-Isoxazoline N-Oxides by Copper-Mediated Radical Annulation of Alkenes with α-Nitrobenzyl Bromides

Masayuki Iwasaki, Yuichi Ikemoto, Yasushi Nishihara

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Copper-mediated [3 + 2] annulation of alkenes with α-nitrobenzyl bromides has been developed. The reaction is promoted simply by a copper salt to produce the corresponding 2-isoxazoline N-oxides with perfect regioselectivity. The present method can be conducted under mild conditions, affording a diverse array of 2-isoxazoline N-oxides. The obtained products can readily be converted to the related heterocycles such as 2-isoxazoline and isoxazole. A radical-polar crossover pathway initiated by single-electron transfer from nitronate to a copper salt is proposed.

Original languageEnglish
Pages (from-to)7577-7580
Number of pages4
JournalOrganic Letters
Volume22
Issue number19
DOIs
Publication statusPublished - Oct 2 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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