Nickel- and Palladium-Catalyzed Coupling of Aryl Fluorosulfonates with Aryl Boronic Acids Enabled by Sulfuryl Fluoride

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• 作者：Patrick S. Hanley ; Matthias S. Ober ; Arkady L. Krasovskiy ; Gregory T. Whiteker ; William J. Kruper
• 刊名：ACS Catalysis
• 出版年：2015
• 出版时间：September 4, 2015
• 年：2015
• 卷：5
• 期：9
• 页码：5041-5046
• 全文大小：398K
• ISSN：2155-5435

文摘

Herein are reported examples of the nickel- and palladium-catalyzed cross-coupling of aryl fluorosulfonates and aryl boronic acids. These reactions occur in good to excellent yields under mild conditions with excellent functional group compatibility employing either Pd(OAc)₂ and inexpensive PPh₃ or the inexpensive and readily available NiCl₂(PCy₃)₂. Importantly, the in situ conversion of phenol derivatives to the corresponding aryl fluorosulfonate by reaction with sulfuryl fluoride and a base and subsequent cross-coupling to form biaryls in a single pot are described. The combination of inexpensive sulfuryl fluoride and efficient catalysts reported in these methodologies will enable economical Suzuki coupling of phenols in pharmaceutical and agrochemical processes.