NHC Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions of Aryl Boronate Esters with Perfluorobenzenes

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• 作者：Jing Zhou ; Johannes H. J. Berthel ; Maximilian W. Kuntze-Fechner ; Alexandra Friedrich ; Todd B. Marder ; Udo Radius
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：81
• 期：13
• 页码：5789-5794
• 全文大小：397K
• 年卷期：0
• ISSN：1520-6904

文摘

An efficient Suzuki–Miyaura cross-coupling reaction of perfluorinated arenes with aryl boronate esters using NHC nickel complexes as catalysts is described. The efficiencies of different boronate esters (p-tolyl-Beg, p-tolyl-Bneop, p-tolyl-Bpin, p-tolyl-Bcat) and the corresponding boronic acid (p-tolyl-B(OH)₂) in this type of cross-coupling reaction were evaluated (eg, ethyleneglycolato; neop, neopentylglycolato; pin, pinacolato; cat, catecholato). Aryl-Beg was shown to be the most reactive boronate ester among those studied. The use of CsF as an additive is essential for an efficient reaction of hexafluorobenzene with aryl neopentylglycolboronates.