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Palladium‐Catalyzed Substitution of Allylic Fluorides
Author(s) -
Hazari Amaruka,
Gouverneur Véronique,
Brown John M.
Publication year - 2009
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.200804310
Subject(s) - allylic rearrangement , palladium , substitution (logic) , catalysis , substitution reaction , chemistry , medicinal chemistry , organic chemistry , computer science , programming language
As unusual substrates for the Tsuji–Trost allylation reaction, allylic fluorides are responsive to palladium‐catalyzed substitution. Their activity towards this reaction fits in the series OCO 2 Me>OBz≫ F ≫OAc. The classic stereoretention mechanism that involves sequential inversions does not operate in this case. Several distinct cases are considered.