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Palladium‐Catalyzed Allylic Fluorination
Author(s) -
Hollingworth Charlotte,
Hazari Amaruka,
Hopkinson Matthew N.,
Tredwell Matthew,
Benedetto Elena,
Huiban Mickael,
Gee Antony D.,
Brown John M.,
Gouverneur Véronique
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.201007307
Subject(s) - allylic rearrangement , tetrahydrofuran , palladium , catalysis , fluoride , chemistry , halogenation , organic chemistry , combinatorial chemistry , inorganic chemistry , solvent
Mild and rapid : The title reaction is presented and its applicability to 18 F radiolabeling is demonstrated (see scheme; TBAF=tetra‐ n ‐butylammonium fluoride, THF=tetrahydrofuran, dba=dibenzylideneacetone). The use of p ‐nitrobenzoate as the leaving group is significant to the success of this catalytic organometallic fluorination process. A range of allylic fluorides were synthesized by this method.