Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates

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• 作者：James Z. Deng ; Daniel V. Paone ; Anthony T. Ginnetti ; Hideki Kurihara ; Spencer D. Dreher ; Steven A. Weissman ; Shaun R. Stauffer ; Christopher S. Burgey
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：January 15, 2009
• 年：2009
• 卷：11
• 期：2
• 页码：345-347
• 全文大小：134K
• 年卷期：v.11,no.2(January 15, 2009)
• ISSN：1523-7052

文摘

The palladium-catalyzed Suzuki−Miyaura reaction has been utilized as one of the most powerful methods for C−C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(I) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope is reported. Use of this methodology affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.