Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF
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Author(s)
Ye, Yuxuan
Takada, Takashi
Buchwald, Stephen Leffler
Date Issued
December 2016
Journal
Angewandte Chemie International Edition
Publisher
Wiley-Blackwell
Citation
Ye, Yuxuan et al. “Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3as an Additive.” Angewandte Chemie International Edition 55, 50 (November 2016): 15559–15563 © 2016 Wiley-VCH Verlag GmbH & Co
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Author's final manuscript
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 (TESCF[subscript 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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1002/ANIE.201608927
