Pd-catalyzed decarboxylative couplings of aryl triazine esters with zinc polyfluorobenzoates

A Pd-catalyzed decarboxylative cross-coupling by 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 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.

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Publication Details

Journal
Synthesis
Published
2025-08-18
DOI
https://doi.org/10.1055/a-2685-9334
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Pd-catalyzed decarboxylative couplings of aryl triazine esters with zinc polyfluorobenzoates

Xue‐Qiang Chu, Zhi‐Liang Shen, Hao Xu, Hao‐Nan Yin et al.
Synthesis
Fluorine in Organic Chemistry
article

Pd-catalyzed decarboxylative couplings of aryl triazine esters with zinc polyfluorobenzoates

Xue‐Qiang Chu, Zhi‐Liang Shen, Hao Xu, Hao‐Nan Yin, Zhou Yun, Hong-Jian Du
article en

Abstract

A Pd-catalyzed decarboxylative cross-coupling by 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 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.

Synthesis
Nanjing Tech University (CN)
Nanjing Tech University
Openalex Percentile: Top 84%
Fluorine in Organic Chemistry
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Pd-catalyzed decarboxylative couplings of aryl triazine esters with zinc polyfluorobenzoates — Xue‐Qiang Chu, Zhi‐Liang Shen, et al. · Synthesis (2025) | TGRS Research Map | TGRS