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The Use of Fluoride as a Leaving Group: S N 2′ Displacement of a CF Bond on 3,3‐Difluoropropenes with Organolithium Reagents To Give Direct Access to Monofluoroalkenes
Author(s) -
Bergeron Maxime,
Johnson Thomas,
Paquin JeanFrançois
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105138
Subject(s) - fluoride , leaving group , reagent , chemistry , nucleophile , lithium fluoride , nucleophilic substitution , combinatorial chemistry , substitution reaction , group (periodic table) , fluorine , lithium (medication) , medicinal chemistry , inorganic chemistry , organic chemistry , catalysis , psychology , psychiatry
Lithium is the key to activate the nucleofuge ability of fluoride in the title transformation (see scheme). This simple and straightforward approach not only provides a practical synthetic method for the preparation of monofluoroalkenes, an important fluorinated motif, but also demonstrates the ability of fluoride to act as a competent leaving group in nucleophilic substitution reactions.