Access to Trifluoromethylketones from Alkyl Bromides and Trifluoroacetic Anhydride by Photocatalysis

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 underdevel...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 62; no. 38; p. e202308732
Main Authors: Du, Hai‐Wu, Du, Yi‐Dan, Zeng, Xian‐Wang, Shu, Wei
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 18.09.2023
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
Aliphatic compounds
Anhydrides
Biological properties
Bromides
Catalysis
Chemistry
Chemistry, Multidisciplinary
Coupling (molecular)
Cross coupling
Fluorine
Halides
Ketones
Photocatalysis
Physical Sciences
Science & Technology
Trifluoroacetic anhydride
Trifluoroacetyl
Anhydrides
CATALYSIS
Photocatalysis
STRATEGY
Radical-Radical Coupling
ALCOHOLS
KETONES
ALKENES
Trifluoroacetylation
FLUORINE
GENERATION
RADICALS
INHIBITORS
Halogen Atom Transfer
DERIVATIVES
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Summary: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).
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202308732