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N-Hydroxybenzimidazole as a structurally modifiable platform forN-oxyl radicals for direct C–H functionalization reactions
Author(s) -
Tomomi Yoshii,
Shigeyuki Tsuzuki,
S. Sakurai,
Ryu Sakamoto,
Julong Jiang,
Miho Hatanaka,
Akira Matsumoto,
Keiji Maruoka
Publication year - 2020
Publication title -
chemical science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 3.687
H-Index - 172
eISSN - 2041-6539
pISSN - 2041-6520
DOI - 10.1039/d0sc02134b
Subject(s) - surface modification , radical , chemistry , catalysis , combinatorial chemistry , organic chemistry
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.