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Visible-Light-Promoted Trifluoromethylthiolation of Styrenes by Dual Photoredox/Halide Catalysis

Lookup NU author(s): Dr Matt HopkinsonORCiD

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Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Herein, we report a new visible-light-promoted strategy to access radical trifluoromethylthiolation reactions by combining halide and photoredox catalysis. This approach allows for the synthesis of vinyl-SCF3 compounds of relevance in pharmaceutical chemistry directly from alkenes under mild conditions with irradiation from household light sources. Furthermore, alkyl-SCF3-containing cyclic ketone and oxindole derivatives can be accessed by radical-polar crossover semi-pinacol and cyclization processes. Inexpensive halide salts play a crucial role in activating the trifluoromethylthiolating reagent towards photoredox catalysis and aid the formation of the SCF3 radical.

Publication metadata

Author(s): Honeker R, Garza-Sanchez RA, Hopkinson MN, Glorius F

Publication type: Article

Publication status: Published

Journal: Chemistry - A European Journal

Year: 2016

Volume: 22

Issue: 13

Pages: 4395-4399

Print publication date: 18/03/2016

Online publication date: 16/02/2016

Acceptance date: 15/01/2016

ISSN (print): 0947-6539

ISSN (electronic): 1521-3765

Publisher: Wiley-VCH Verlag

URL: https://doi.org/10.1002/chem.201600190

DOI: 10.1002/chem.201600190

PubMed id: 26880666

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