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 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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). |
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ISSN: | 1523-7060 1523-7052 1523-7052 |
DOI: | 10.1021/acs.orglett.4c01898 |