N-Hydroxybenzimidazole as a structurally modifiable platform forN-oxyl radicals for direct C-H functionalization reactions

Tomomi Yoshii, Saori Tsuzuki, Shunya Sakurai, Ryu Sakamoto, Julong Jiang, Miho Hatanaka, Akira Matsumoto, Keiji Maruoka

Research output: Contribution to journalArticle

Abstract

Methods for direct functionalization of C-H bonds mediated byN-oxyl radicals constitute a powerful tool in modern organic synthesis. While severalN-oxyl radicals have been developed to date, the lack of structural diversity for these species has hampered further progress in this field. Here we designed a novel class ofN-oxyl radicals based onN-hydroxybenzimidazole, and applied them to the direct C-H functionalization reactions. The flexibly modifiable features of these structures enabled facile tuning of their catalytic performance. Moreover, with these organoradicals, we have developed a metal-free approach for the synthesis of acyl fluoridesviadirect C-H fluorination of aldehydes under mild conditions.

Original languageEnglish
Pages (from-to)5772-5778
Number of pages7
JournalChemical Science
Volume11
Issue number22
DOIs
Publication statusPublished - 2020 Jun 14

ASJC Scopus subject areas

  • Chemistry(all)

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