Catalytic Generation of Radicals from Nitroalkanes

Myuto Kashihara, Kohie Kosaka, Naoki Matsushita, Shunta Notsu, Ayumi Osawa, Yoshiaki Nakao

Research output: Contribution to journalArticlepeer-review

Abstract

A new protocol for the catalytic denitrative generation of radicals from nitroalkanes was disclosed. 9-Fluorenol acts as a single-electron-transfer catalyst that reduces nitroalkanes to promote the C-NO2 bond cleavage, followed by the formation of alkyl radicals. The obtained radicals participate in diverse transformations such as hydrogenation, Giese addition, spirocyclization, and Minisci reactions by using appropriate trapping reagents. The present system outperforms conventional methods using tin hydrides in terms of cost, toxicity, and experimental operations.

Original languageEnglish
JournalSynlett
DOIs
Publication statusAccepted/In press - 2022

Keywords

  • 9-fluorenol
  • denitration
  • Nitroalkane
  • organocatalysis
  • radical
  • single-electron transfer

ASJC Scopus subject areas

  • Organic Chemistry

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