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Fluorobis(phenylsulfonyl)methane: A Fluoromethide Equivalent and Palladium‐Catalyzed Enantioselective Allylic Monofluoromethylation
Author(s) -
Fukuzumi Takeo,
Shibata Norio,
Sugiura Masayoshi,
Yasui Hiroyuki,
Nakamura Shuichi,
Toru Takeshi
Publication year - 2006
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.200600625
Subject(s) - allylic rearrangement , palladium , enantioselective synthesis , catalysis , chemistry , methane , organic chemistry , combinatorial chemistry
Selective introduction of fluorine : Monofluoromethylation with the fluoromethide equivalent fluorobis(phenylsulfonyl)methane ( 1 ) was crucial in the syntheses of the pharmacologically important compounds monofluorinated ( S )‐ibuprofen (( S )‐ 2 ) and 5‐deoxy‐5‐fluoro‐β‐ D ‐carbaribofuranose ( 3 ). The key step was a palladium‐catalyzed allylic monofluoromethylation reaction.