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Access to Trifluoromethylketones from Alkyl Bromides and Trifluoroacetic Anhydride by Photocatalysis.

Authors :
Du HW
Du YD
Zeng XW
Shu W
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Sep 18; Vol. 62 (38), pp. e202308732. Date of Electronic Publication: 2023 Aug 10.
Publication Year :
2023

Abstract

Aliphatic trifluoromethyl ketones are a type of unique fluorine-containing subunit which play a significant role in altering the physical and biological properties of molecules. Catalytic methods to provide direct access to aliphatic trifluoromethyl ketones are highly desirable yet remain underdeveloped, partially owing to the high reactivity and instability of trifluoroacetyl radical. Herein, we report a photocatalytic synthesis of trifluoromethyl ketones from alkyl bromides with trifluoroacetic anhydride. The reaction features dual visible-light and halogen-atom-transfer catalysis, followed by an enabling radical-radical cross-coupling of an alkyl radical with a stabilized trifluoromethyl radical. The reaction provides straightforward access to aliphatic trifluoromethyl ketones from readily available and cost-effective alkyl halides and trifluoroacetic anhydride (TFAA).<br /> (© 2023 Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1521-3773
Volume :
62
Issue :
38
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
37534823
Full Text :
https://doi.org/10.1002/anie.202308732