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Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3 as an Additive.


ABSTRACT: 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 (TESCF3 ) 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.

SUBMITTER: Ye Y 

PROVIDER: S-EPMC5198716 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF<sub>3</sub> as an Additive.

Ye Yuxuan Y   Takada Takashi T   Buchwald Stephen L SL  

Angewandte Chemie (International ed. in English) 20161115 50


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<sub>3</sub> ) was found to effectively address this problem and resulted in drastically improved regioselectivities in this palladium-catalyzed fluorination  ...[more]

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