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

An unexpected three-component reaction of quinoxalin-2(1 H )-ones, tert -butyl peroxybenzoate (TBPB), and hexafluoroisopropanol (HFIP) is described. Under CuBr-catalyzed and TBPB-oxidized conditions, a variety of hydroxyhexafluoroisobutylated quinoxalin-2(1 H )-ones were formed. Furthermore, the fir...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-10, Vol.56 (84), p.1285-1288
Main Authors: Su, Hai-Yan, Zhu, Xiao-Lei, Huang, Yangen, Xu, Xiu-Hua, Qing, Feng-Ling
Format: Article
Language:English
Subjects:
Crystallography
Oxidizing agents
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Summary:An unexpected three-component reaction of quinoxalin-2(1 H )-ones, tert -butyl peroxybenzoate (TBPB), and hexafluoroisopropanol (HFIP) is described. Under CuBr-catalyzed and TBPB-oxidized conditions, a variety of hydroxyhexafluoroisobutylated quinoxalin-2(1 H )-ones were formed. Furthermore, the first hexafluoroisopropoxylation of the quinoxalin-2(1 H )-ones with HFIP is also demonstrated with Cu 2 O as the catalyst and PhI(OAc) 2 as the oxidant. These new transformations of HFIP furnish previously unknown and potentially useful fluorinated quinoxalin-2(1 H )-one derivatives. New applications of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) were reported in the copper-catalyzed chemoselective C-H hydroxyhexafluoroisobutylation and hexafluoroisopropoxylation of quinoxalin-2(1 H )-ones.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc05623e