Hydroximoyl fluorides as the precursors of nitrile oxides: synthesis, stability and [3+2]-cycloaddition with alkynes

The transformation of hydroximoyl fluorides to nitrile oxides for [3 + 2]-cycloaddition with alkynes has been achieved for the first time. The hydroximoyl fluorides used in this work appeared to be not stable, which was proved by a series of experiments. A DFT calculation was performed to better und...

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Published inOrganic & biomolecular chemistry Vol. 16; no. 47; pp. 9211 - 9217
Main Authors Gao, Feng-Teng, Fang, Zheng, Su, Rui-Rui, Rui, Pei-Xin, Hu, Xiang-Guo
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 05.12.2018
Royal Society of Chemistry
Subjects
Alkynes
Chemical synthesis
Chemistry
Chemistry, Organic
Crystallography
Cycloaddition
Fluorides
Fluorination
Oxides
Physical Sciences
Purification
Science & Technology
Stability
FUNCTIONALIZATION
SUBSTITUTION
OXIMES
REAGENTS
MECHANISM
GEM-DIFLUOROALKENES
GENERATION
SALTS
F BOND ACTIVATION
HYDRODEFLUORINATION
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Summary:The transformation of hydroximoyl fluorides to nitrile oxides for [3 + 2]-cycloaddition with alkynes has been achieved for the first time. The hydroximoyl fluorides used in this work appeared to be not stable, which was proved by a series of experiments. A DFT calculation was performed to better understand the properties of hydroximoyl fluorides. Although not stable, the hydroximoyl fluorides could be successfully converted to the corresponding nitrile oxides for in situ [3 + 2]-cycloaddition with alkynes to yield the iso-xazoles. Furthermore, it was feasible to conduct [3 + 2]-cycloaddition reaction without purification after the synthesis of hydroximoyl fluorides from gem-difluoroalkenes. By investigating a class of interesting yet previously rarely explored fluorinated compounds, this work sheds new light on the stability and reactivity of a C-F bond on a C=N double bond.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02721h