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Article Abstract
A palladium-catalyzed decarboxylative cross-coupling of zinc polyfluorobenzoates with aryl fluorosulfates, which proceeded efficiently via C-O bond cleavage to afford the corresponding polyfluorinated biaryls in moderate-to-good yields, was developed. The reactions exhibited both good substrate scope and broad functional group compatibility, and it could be scaled-up easily. The synthetic simplicity and practicability of the reaction was further demonstrated by one-pot manipulation by directly mixing polyfluorobenzoic acid and Zn(OH) in the coexistence of aryl fluorosulfate and a palladium catalyst in one flask. Further studies showed that aryl fluorosulfate is more robust than other aryl halides and pseudohalides as a arylating reagent, and zinc polyfluorobenzoate is a more effective decarboxylative polyfluoroarylating agent than their magnesium and potassium counterparts.
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Pd-catalyzed decarboxylative coupling of zinc polyfluorobenzoate with aryl imidazolylsulfonate for polyfluorinated biaryl synthesis.
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We report here an efficient decarboxylative cross-coupling of zinc polyfluorobenzoates with aryl imidazolylsulfonates under palladium catalysis, which proceeded effectively 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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Article Synopsis
- A new method using phosphine to promote the reaction between nitro compounds and Grignard reagents leads to the efficient creation of diarylamines, which are important in pharmaceuticals.
- The reaction allows for the inclusion of challenging aliphatic nitro compounds, resulting in α-arylation alongside reductive coupling to produce useful α-arylated arylamines.
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