N-Hydroxybenzimidazole as a structurally modifiable platform for N-oxyl radicals for direct C-H functionalization
Tomomi Yoshii1, Saori Tsuzuki1, Shunya Sakurai1
1Department of Chemistry , Graduate School of Science , Kyoto University , Sakyo , Kyoto 606-8502 , Japan .
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.
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