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Palladium‐Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF 3 as an Additive
Author(s) -
Ye Yuxuan,
Takada Takashi,
Buchwald Stephen L.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201608927
Subject(s) - palladium , regioselectivity , catalysis , chemistry , silane , fluoride , organic chemistry , combinatorial chemistry , inorganic chemistry
A method for the palladium‐catalyzed fluorination of cyclic vinyl triflates has been developed. As with several previous palladium‐catalyzed fluorination reactions using fluoride salts, controlling the regioselectivity presented a challenge in developing a practical synthetic procedure. The addition of triethyl(trifluoromethyl)silane (TESCF 3 ) was found to effectively address this problem and resulted in drastically improved regioselectivities in this palladium‐catalyzed fluorination reaction. This discovery, along with the use of a new biarylphosphine ligand, allowed for the development of an efficient and highly regioselective protocol for the fluorination of vinyl triflates. This method is compatible with a range of sensitive functional groups and provides access to five‐, six‐, and seven‐membered cyclic vinyl fluorides.