N-Hydroxybenzimidazole as a structurally modifiable platform for N-oxyl radicals for direct C–H functionalization reactions. Issue 22 (27th May 2020)

• Record Type: Journal Article
• Authors: Yoshii, Tomomi; Tsuzuki, Saori; Sakurai, Shunya; Sakamoto, Ryu; Jiang, Julong; Hatanaka, Miho; Matsumoto, Akira; Maruoka, Keiji
• Is Part Of: Chemical science. Volume 11:Issue 22(2020)
• Page Start: 5772
• Page End: 5778
• Publication Date: 2020-05-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc02134b
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A novel class of N -oxy radicals based on flexibly modifiable N -hydroxybenzimidazole skeleton was designed and applied to C–H functionalization reactions. Abstract : Methods for direct functionalization of C–H bonds mediated by N -oxyl radicals constitute a powerful tool in modern organic synthesis. While several N -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 of N -oxyl radicals based on N -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 fluorides via direct C–H fluorination of aldehydes under mild conditions.