Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 65, Pages 16460-16465Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704322
Keywords
C-F activation; difluoroalkenes; lanthanides; pentadienyl complexes; spirocycles
Categories
Funding
- ANR [ANR-15-CE29-0020-01 ACTIV-CF-LAN]
- CEFIPRA [4505-1]
- CNRS
- Universite de Reims
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Heavy metal on Lewis acid: The combination of lanthanide metals and AlCl3 has been employed for selective single C-F activation in benzofulvenes comprising an exocyclic CF3 substituent. Intermediate epsilon,epsilon-difluorinated metal-dienyl species react with a large variety of aldehydes in a highly regio- and diastereoselective fashion to afford 1,1-disubstituted indenes bearing a difluorovinyl group. These new building blocks have been further transformed through a hydrogenation-cyclization process into fluorinated heterocyclic spiro compounds.
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