Visible-Light-Induced DDQ-Catalyzed Fluorocarbamoylation Using CF3SO2Na and Oxygen

Visible-Light-Induced DDQ-Catalyzed Fluorocarbamoylation Using CF3SO2Na and Oxygen

The synthesis of carbamoyl fluorides via visible-light induced DDQ catalysis of secondary amines is described. This protocol employs sodium trifluorosulfinate and molecular oxygen for the in situ generation of carbonyl difluoride, which is reacted with amines to afford the corresponding carbamoyl fl...

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Bibliographic Details
Published in:Organic letters Vol. 25; no. 48; pp. 8558 - 8563
Main Authors: Cho, Huijeong, Jang, Seonga, Lee, Kangjoo, Cha, Dohoon, Min, Sun-Joon
Format: Journal Article
Language:English
Published: 08-12-2023
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Summary:The synthesis of carbamoyl fluorides via visible-light induced DDQ catalysis of secondary amines is described. This protocol employs sodium trifluorosulfinate and molecular oxygen for the in situ generation of carbonyl difluoride, which is reacted with amines to afford the corresponding carbamoyl fluorides efficiently. Moreover, carbamoyl fluorides are easily transformed to synthetically useful carbonyl compounds under mild reaction conditions.
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ISSN:1523-7052
DOI:10.1021/acs.orglett.3c03335