Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds
AbstractIn this review, we summarize our recent development of palladium(0)-catalyzed cross-coupling reactions of perfluoro organic compounds with organometallic reagents. The oxidative addition of a C–F bond of tetrafluoroethylene (TFE) to palladium(0) was promoted by the addition of lithium iodide, affording a trifluorovinyl palladium(II) iodide. Based on this finding, the first palladium-catalyzed cross-coupling reaction of TFE with diarylzinc was developed in the presence of lithium iodide, affording α,β,β-trifluorostyrene derivatives in excellent yield. This coupling reaction was expanded to the novel Pd(0)/PR3-catalyzed cross-coupling reaction of TFE with arylboronates. In this reaction, the trifluorovinyl palladium(II) fluoride was a key reaction intermediate that required neither an extraneous base to enhance the reactivity of organoboronates nor a Lewis acid additive to promote the oxidative addition of a C–F bond. In addition, our strategy utilizing the synergetic effect of Pd(0) and lithium iodide could be applied to the C–F bond cleavage of unreactive hexafluorobenzene (C6F6), leading to the first Pd(0)-catalyzed cross-coupling reaction of C6F6 with diarylzinc compounds. View Full-Text
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Ohashi, M.; Ogoshi, S. Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds. Catalysts 2014, 4, 321-345.
Ohashi M, Ogoshi S. Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds. Catalysts. 2014; 4(3):321-345.Chicago/Turabian Style
Ohashi, Masato; Ogoshi, Sensuke. 2014. "Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds." Catalysts 4, no. 3: 321-345.