Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 45, Pages 15261-15266Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201303248
Keywords
carbenes; difluorocyclopropanation; difluoro-olefination; fluorine; ylides
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Funding
- National Natural Science Foundation [21032006, 21172240]
- 973 Program of China [2012CBA01200]
- Chinese Academy of Sciences
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The interconversion between difluoromethylene ylide and difluorocarbene is described. The difluoromethylene ylide precursor, Ph3P+CF2CO2-, could be turned into an efficient difluorocarbene reagent, whereas the classical difluorocarbene reagents, HCF2Cl and FSO2CF2CO2TMS, could generate highly reactive difluoromethylene ylide. Thus the Wittig difluoro-olefination and difluorocyclopropanation could be selectively realized by using the same reagent. In addition, the ylides obtained from different carbene sources showed different reactivity in Wittig reactions.
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