Oxidation of difluorocarbene and subsequent trifluoromethoxylation

As a versatile intermediate, difluorocarbene is an electron-deficient transient species, meaning that its oxidation would be challenging. Herein we show that the oxidation of difluorocarbene could occur smoothly to generate carbonyl fluoride. The oxidation process is confirmed by successful trifluor...

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Published inNature communications Vol. 10; no. 1; pp. 5362 - 8
Main Authors Yu, Jiao, Lin, Jin-Hong, Yu, Donghai, Du, Ruobing, Xiao, Ji-Chang
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 25.11.2019
Nature Publishing Group
Nature Portfolio
Subjects
140/131
140/58
639/638/403/933
639/638/403/934
639/638/549/2264
Carbonyl compounds
Carbonyls
Fluorides
Humanities and Social Sciences
multidisciplinary
Oxidation
Oxidation process
Science
Science (multidisciplinary)
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Summary:As a versatile intermediate, difluorocarbene is an electron-deficient transient species, meaning that its oxidation would be challenging. Herein we show that the oxidation of difluorocarbene could occur smoothly to generate carbonyl fluoride. The oxidation process is confirmed by successful trifluoromethoxylation, 18 O-trifluoromethoxylation, the observation of AgOCF 3 species, and DFT calculations. Difluorocarbene is a versatile and efficient intermediate for fluorine incorporation. Here, the authors show that difluorocarbene can be oxidized to carbonyl fluoride and this process is confirmed in 18 O-trifluoromethoxylation reactions, by observation of AgOCF 3 species and theory.
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ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-019-13359-z