Site-Selective Photobromination of O‑Acetylated Carbohydrates in Benzotrifluoride

Ferrier photobromination enables direct synthetic access to valuable 5-C-bromosugars but has limitations that restrict its broader use. The reaction is typically conducted in CCl4 heated at reflux with irradiation by broad spectrum, energy-inefficient heat lamps. Herein, we demonstrate that the reac...

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Veröffentlicht in:Organic letters 2024-07, Vol.26 (28), p.5956-5960
Hauptverfasser: Zhang, Guoqing, See, Nicholas W., Wimmer, Norbert, Godinez, Michael J., Cameron, Scott A., Furneaux, Richard H., Ferro, Vito
Format: Artikel
Sprache:eng
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Zusammenfassung:Ferrier photobromination enables direct synthetic access to valuable 5-C-bromosugars but has limitations that restrict its broader use. The reaction is typically conducted in CCl4 heated at reflux with irradiation by broad spectrum, energy-inefficient heat lamps. Herein, we demonstrate that the reaction proceeds rapidly and efficiently with PhCF3 as a safe and environmentally benign alternative to CCl4 at mild temperatures (≤40 °C) inside a compact photoreactor fitted with purple light-emitting diodes (LEDs).
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01898