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Generation of ϵ,ϵ‐Difluorinated Metal‐Pentadienyl Species through Lanthanide‐Mediated C−F Activation
Author(s) -
Kumar Tarun,
Massicot Fabien,
Harakat Dominique,
Chevreux Sylviane,
Martinez Agathe,
Bordolinska Klaudia,
Preethalayam Preethanuj,
Kokkuvayil Vasu Radhakrishnan,
Behr JeanBernard,
Vasse JeanLuc,
Jaroschik Florian
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704322
Subject(s) - substituent , lanthanide , chemistry , metal , lewis acids and bases , medicinal chemistry , stereochemistry , organic chemistry , catalysis , ion
Heavy metal on Lewis acid : The combination of lanthanide metals and AlCl 3 has been employed for selective single C−F activation in benzofulvenes comprising an exocyclic CF 3 substituent. Intermediate ϵ,ϵ‐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.