Fluorobis(phenylsulfonyl)methane: A Fluoromethide Equivalent and Palladium‐Catalyzed Enantioselective Allylic Monofluoromethylation | Zendy

Fukuzumi Takeo | Zendy; Shibata Norio | Zendy; Sugiura Masayoshi | Zendy; Yasui Hiroyuki | Zendy; Nakamura Shuichi | Zendy; Toru Takeshi | Zendy

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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.

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