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Issue 84, 2020
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Copper-catalyzed chemoselective C–H functionalization of quinoxalin-2(1H)-ones with hexafluoroisopropanol

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Abstract

An unexpected three-component reaction of quinoxalin-2(1H)-ones, tert-butyl peroxybenzoate (TBPB), and hexafluoroisopropanol (HFIP) is described. Under CuBr-catalyzed and TBPB-oxidized conditions, a variety of hydroxyhexafluoroisobutylated quinoxalin-2(1H)-ones were formed. Furthermore, the first hexafluoroisopropoxylation of the quinoxalin-2(1H)-ones with HFIP is also demonstrated with Cu2O as the catalyst and PhI(OAc)2 as the oxidant. These new transformations of HFIP furnish previously unknown and potentially useful fluorinated quinoxalin-2(1H)-one derivatives.

Graphical abstract: Copper-catalyzed chemoselective C–H functionalization of quinoxalin-2(1H)-ones with hexafluoroisopropanol

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Supplementary files

Article information


Submitted
18 Aug 2020
Accepted
15 Sep 2020
First published
15 Sep 2020

Chem. Commun., 2020,56, 12805-12808
Article type
Communication

Copper-catalyzed chemoselective C–H functionalization of quinoxalin-2(1H)-ones with hexafluoroisopropanol

H. Su, X. Zhu, Y. Huang, X. Xu and F. Qing, Chem. Commun., 2020, 56, 12805
DOI: 10.1039/D0CC05623E

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