Site-Selective Photobromination of O‑Acetylated Carbohydrates in Benzotrifluoride

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
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container_end_page 5960
container_issue 28
container_start_page 5956
container_title Organic letters
container_volume 26
creator Zhang, Guoqing
See, Nicholas W.
Wimmer, Norbert
Godinez, Michael J.
Cameron, Scott A.
Furneaux, Richard H.
Ferro, Vito
description 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).
doi_str_mv 10.1021/acs.orglett.4c01898
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title Site-Selective Photobromination of O‑Acetylated Carbohydrates in Benzotrifluoride
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