Pd-catalyzed decarboxylative coupling of zinc polyfluorobenzoate with aryl imidazolylsulfonate for polyfluorinated biaryl synthesis

We report here an efficient decarboxylative cross-coupling of zinc polyfluorobenzoates with aryl imidazolylsulfonates under palladium catalysis, which proceeded effectively <i>via</i> C-O bond cleavage to afford the corresponding valuable polyfluorinated biaryls in moderate to good yields, exhibiting both reasonable substrate scope and broad functional group tolerance. In addition, late-stage functionalization of bioactive molecules and an amino acid-derived compound and scaled-up synthesis could be accomplished as well. Further exploration revealed that zinc polyfluorobenzoates are more vibrant than their potassium, sodium, and magnesium counterparts as a polyfluoroarylating reagent.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00528k
Citations
3
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
2.81
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article

Pd-catalyzed decarboxylative coupling of zinc polyfluorobenzoate with aryl imidazolylsulfonate for polyfluorinated biaryl synthesis

Weidong Rao, Xue‐Qiang Chu, Zhi‐Liang Shen, Hao Xu et al.
3 citations
Organic & Biomolecular Chemistry
Catalytic Cross-Coupling Reactions
2.81
article

Pd-catalyzed decarboxylative coupling of zinc polyfluorobenzoate with aryl imidazolylsulfonate for polyfluorinated biaryl synthesis

Weidong Rao, Xue‐Qiang Chu, Zhi‐Liang Shen, Hao Xu, Chao Gui, Hui Tian, Chengping Miao, Zhou Yun
article en
3 citations

Abstract

We report here an efficient decarboxylative cross-coupling of zinc polyfluorobenzoates with aryl imidazolylsulfonates under palladium catalysis, which proceeded effectively <i>via</i> C-O bond cleavage to afford the corresponding valuable polyfluorinated biaryls in moderate to good yields, exhibiting both reasonable substrate scope and broad functional group tolerance. In addition, late-stage functionalization of bioactive molecules and an amino acid-derived compound and scaled-up synthesis could be accomplished as well. Further exploration revealed that zinc polyfluorobenzoates are more vibrant than their potassium, sodium, and magnesium counterparts as a polyfluoroarylating reagent.

Organic & Biomolecular ChemistryVol. 23(23)
Nanjing Tech University (CN), Nanjing Forestry University (CN), Jiaxing University (CN)
Openalex Percentile: Top 11%
Catalytic Cross-Coupling Reactions
2.81
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Pd-catalyzed decarboxylative coupling of zinc polyfluorobenzoate with aryl imidazolylsulfonate for polyfluorinated biaryl synthesis — Weidong Rao, Xue‐Qiang Chu, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS