Generation of ϵ, ϵ‐Difluorinated Metal‐Pentadienyl Species through Lanthanide‐Mediated C−F Activation. Issue 65 (9th November 2017)

• Record Type: Journal Article
• Authors: Kumar, Tarun; Massicot, Fabien; Harakat, Dominique; Chevreux, Sylviane; Martinez, Agathe; Bordolinska, Klaudia; Preethalayam, Preethanuj; Kokkuvayil Vasu, Radhakrishnan; Behr, Jean‐Bernard; Vasse, Jean‐Luc; Jaroschik, Florian
• Is Part Of: Chemistry. Volume 23:Issue 65(2017)
• Page Start: 16460
• Page End: 16465
• Publication Date: 2017-11-09
• Subjects: C−F activation -- difluoroalkenes -- lanthanides -- pentadienyl complexes -- spirocycles; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201704322
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 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. Abstract : Heavy metal on Lewis acid : Lanthanides and AlCl3 have been employed for selective single C−F activation in benzofulvenes. 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.