Premium
A Convenient Route to Tetraalkylammonium Perfluoroalkoxides from Hydrofluoroethers
Author(s) -
Jelier Benson J.,
Howell Jon L.,
Montgomery Craig D.,
Leznoff Daniel B.,
Friesen Chadron M.
Publication year - 2015
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.201410639
Subject(s) - chemistry , alkylation , solvent , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Hydrofluoroethers are shown to alkylate tertiary amines readily under solvent‐free conditions, affording valuable tetraalkylammonium perfluoroalkoxides bearing α‐fluorines. The reaction of R F CF 2 OCH 3 (R F =CF 2 CF 3 , CF 2 CF 2 CF 3 , and CF(CF 3 ) 2 ) with NR 1 R 2 R 3 produces twenty new α‐perfluoroalkoxides, [(CH 3 )NR 1 R 2 R 3 ][R F CF 2 O] under mild conditions. These α‐perfluoroalkoxides are easy to handle, thermally stable, and can be used for the perfluoroalkoxylation of benzyl bromides.