Generation of ϵ,ϵ-Difluorinated Metal-Pentadienyl Species through Lanthanide-Mediated C-F Activation
Tarun Kumar1, Fabien Massicot1, Dominique Harakat1
1Institut de Chimie Moléculaire de Reims (CNRS UMR 7312), Université de Reims Champagne-Ardenne, BP 1039, 51687, Reims Cedex 2, France.
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.
More Related Videos
09:45Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Related Concept Videos
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
ortho–para-Directing Deactivators: Halogens
Halogens
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Electron Affinity
