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

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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.

Graphical abstract: N-Hydroxybenzimidazole as a structurally modifiable platform for N-oxyl radicals for direct C–H functionalization reactions

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Article information


Submitted
15 Apr 2020
Accepted
16 May 2020
First published
18 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

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

T. Yoshii, S. Tsuzuki, S. Sakurai, R. Sakamoto, J. Jiang, M. Hatanaka, A. Matsumoto and K. Maruoka, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC02134B

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