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2‐Fluoro‐1,3‐benzodithiole‐1,1,3,3‐tetraoxide: A Reagent for Nucleophilic Monofluoromethylation of Aldehydes
Author(s) -
Furukawa Tatsuya,
Goto Yosuke,
Kawazoe Jumpei,
Tokunaga Etsuko,
Nakamura Shuichi,
Yang Yudong,
Du Hongguang,
Kakehi Akikazu,
Shiro Motoo,
Shibata Norio
Publication year - 2010
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.200906866
Subject(s) - reagent , nucleophile , chemistry , organic chemistry , combinatorial chemistry , catalysis
Matter of choice : The title compound (FBDT), a cyclic analogue of 1‐fluorobis(phenylsulfonyl)methane (FBSM), was developed as a reagent for the nucleophilic monofluoromethylation of aldehydes. By choice of an appropriate base it is possible to achieve selective 1,2‐ or 1,4‐addition of FBDT to conjugated aldehydes. The method was applied to the synthesis of a fluorinated isostere of osmundalactone.