A C鈥揌 Borylation Approach to Suzuki鈥揗iyaura Coupling of Typically Unstable 2鈥揌eteroaryl and Polyfluorophenyl Boronates

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• 作者：Daniel W. Robbins ; John F. Hartwig
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：August 17, 2012
• 年：2012
• 卷：14
• 期：16
• 页码：4266-4269
• 全文大小：287K
• 年卷期：v.14,no.16(August 17, 2012)
• ISSN：1523-7052

文摘

A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C鈥揌 borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.