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cis ‐Specific Hydrofluorination of Alkenylarenes under Palladium Catalysis through an Ionic Pathway
Author(s) -
Emer Enrico,
Pfeifer Lukas,
Brown John M.,
Gouverneur Véronique
Publication year - 2014
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.201310056
Subject(s) - palladium , catalysis , ionic bonding , chemistry , enantioselective synthesis , ionic liquid , combinatorial chemistry , reaction mechanism , organic chemistry , ion
This paper describes the hydrofluorination of alkenes through sequential H − and F + addition under palladium catalysis. The reaction is cis specific, thus providing access to benzylic fluorides. The mechanism of this reaction involves an ionic pathway and is distinct from known hydrofluorinations involving radical intermediates. The first catalytic enantioselective hydrofluorination is also disclosed.