Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 68, Pages 17932-17935Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201805054
Keywords
aromatic substitution; bond activation; carbocations; cyclopropane; fluorine; trifluoromethyl group
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Funding
- JSPS KAKENHI [JP18H04234, JP16H04105]
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The selective activation of one C-F bond (single activation) of the CF3 group on cyclopropanes was achieved for the first time. When (trifluoromethyl)cyclopropanes were treated with arenes, allylsilanes, silyl enol ethers, or hydrosilanes in the presence of Me2AlCl, fluoride elimination and the subsequent ring opening proceeded to afford 4,4-difluorohomoallylated products. In the absence of external nucleophiles, an alkyl group of AlR3 was effectively introduced to provide the corresponding 1,1-difluoroalkenes.
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