Beyond Directed ortho Metalation: Ru-Catalyzed CAr鈥揙 Activation/Cross-Coupling Reaction by Amide Chelation

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• 作者：Yigang Zhao ; Victor Snieckus
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：August 13, 2014
• 年：2014
• 卷：136
• 期：32
• 页码：11224-11227
• 全文大小：329K
• ISSN：1520-5126

文摘

Disclosed is a new, catalytic, and general methodology for the chemical synthesis of biaryl, heterobiaryl, and polyaryl molecules by the cross-coupling of o-methoxybenzamides with aryl boroneopentylates. The reaction is based on the activation of the unreactive C鈥揙Me bond by the proximate amide directing group using catalytic RuH<sub>2sub>(CO)(PPh<sub>3sub>)<sub>3sub> conditions. A one-step, base-free coupling process is thereby established that has the potential to supersede the useful two-step directed ortho metalation/cross-coupling reaction involving cryogenic temperature and strong base conditions. High regioselectivity, orthogonality with the Suzuki鈥揗iyaura reaction, operational simplicity, minimum waste, and convenient scale-up make these reactions suitable for industrial applications.