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Catalysts 2014, 4(3), 321-345; https://doi.org/10.3390/catal4030321

Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds

1
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
2
JST, Advanced Catalytic Transformation program for Carbon utilization (ACT-C), Suita, Osaka 565-0871, Japan
*
Authors to whom correspondence should be addressed.
Received: 25 June 2014 / Revised: 19 August 2014 / Accepted: 21 August 2014 / Published: 10 September 2014
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
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Abstract

In 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
Keywords: C–F bond activation; palladium; perfluoroalkene; perfluoroarene; cross-coupling; diarylzinc; arylboronate C–F bond activation; palladium; perfluoroalkene; perfluoroarene; cross-coupling; diarylzinc; arylboronate
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Ohashi, M.; Ogoshi, S. Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds. Catalysts 2014, 4, 321-345.

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