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Synthesis 2025; 57(21): 3315-3324
DOI: 10.1055/a-2685-9334
DOI: 10.1055/a-2685-9334
Paper
Pd-Catalyzed Decarboxylative Couplings of Aryl Triazine Esters With Zinc Polyfluorobenzoates
Authors
Funding Information The authors gratefully acknowledge the financial support from Nanjing Tech University (Start-up Grant No. 39837118).
Dedication
Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.
Abstract
A Pd-catalyzed decarboxylative cross-coupling using zinc polyfluorobenzoates as robust polyfluoroarylating agents and aryl triazine esters as effective benzoylating reagents was realized, enabling the facile assembly of a wide array of valuable polyfluorinated aryl ketones in moderate to good yields. A variety of functional groups could be well tolerated in the protocol, and the reaction could be scaled up as well. Especially noteworthy is that one-pot reaction by directly adding polyfluorobenzoic acid and Zn(OH)2 to the decarboxylative reaction as a precursor to in situ form zinc polyfluorobenzoate could also be successfully achieved, thereby providing a more practical, step-economic, and cost-effective approach for accessing polyfluorinated aryl ketones. Control experiments showed that zinc pentafluorobenzoate was superior to other metallic counterparts.
Keywords
Palladium catalysis - Decarboxylative reaction - Zinc polyfluorobenzoate - Aryl triazine ester - Polyfluorinated aryl ketonePublication History
Received: 24 July 2025
Accepted after revision: 18 August 2025
Accepted Manuscript online:
18 August 2025
Article published online:
30 September 2025
© 2025. Thieme. All rights reserved.
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For other methods for the synthesis of polyfluorinated aryl ketones, see:
For selected recent examples of carbonylative reactions, see: