Palladium-Catalyzed, Direct Boronic Acid Synthesis from Aryl Chlorides: A Simplified Route to Diverse Boronate Ester Derivatives
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- 作者：Gary A. Molander ; Sarah L. J. Trice ; Spencer D. Dreher
- 刊名：Journal of the American Chemical Society
- 出版年：2010
- 出版时间：December 22, 2010
- 年：2010
- 卷：132
- 期：50
- 页码：17701-17703
- 全文大小：199K
- 年卷期：v.132,no.50(December 22, 2010)
- ISSN：1520-5126
文摘
Although much current research focuses on developing new boron reagents and identifying robust catalytic systems for the cross-coupling of these reagents, the fundamental preparations of the nucleophilic partners (i.e., boronic acids and derivatives) has been studied to a lesser extent. Most current methods to access boronic acids are indirect and require harsh conditions or expensive reagents. A simple and efficient palladium-catalyzed, direct synthesis of arylboronic acids from the corresponding aryl chlorides using an underutilized reagent, tetrahydroxydiboron B2(OH)4, is reported. To ensure preservation of the carbon−boron bond, the boronic acids were efficiently converted to the trifluoroborate derivatives in good to excellent yields without the use of a workup or isolation. Further, the intermediate boronic acids can be easily converted to a wide range of useful boronates. Finally, a two-step, one-pot method was developed to couple two aryl chlorides efficiently in a Suzuki−Miyaura-type reaction.