Flow electrosynthesis for efficient O-trifluoromethylation of electron-deficient phenols

[Display omitted] •Efficient and sustainable O-trifluoromethylation of electron-poor phenols.•First approach by combination of electrochemistry with flow chemistry.•Electrical current as inexpensive, safe, and green reagent.•Easy access to otherwise hardly accessible compounds. A sustainable strateg...

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Veröffentlicht in:Electrochemistry communications 2023-09, Vol.154, p.107545, Article 107545
Hauptverfasser: Bernd, Johannes, Terfort, Andreas
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] •Efficient and sustainable O-trifluoromethylation of electron-poor phenols.•First approach by combination of electrochemistry with flow chemistry.•Electrical current as inexpensive, safe, and green reagent.•Easy access to otherwise hardly accessible compounds. A sustainable strategy for O-trifluoromethylation of electron-deficient phenols by combining electrochemical synthesis with flow technology is presented. The reaction is optimized by screening experiments to establish a fast and efficient flow protocol. Simultaneous anodic oxidation of Langlois reagent and the phenols in a micro flow cell leads to direct preparation of trifluoromethyl ethers in yields up to 90%. This one-step protocol is tolerant of several functional groups, shows good regioselectivity and works without any chemical oxidants and catalysts by using electrical current as an inexpensive and sustainable reagent.
ISSN:1388-2481
1873-1902
DOI:10.1016/j.elecom.2023.107545