An Adventure in Sustainable Cross-Coupling of Phenols and Derivatives via Carbon–Oxygen Bond Cleavage

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• 作者：Huiying Zeng ; Zihang Qiu ; Alejandra Domínguez-Huerta ; Zoë Hearne ; Zhengwang Chen ; Chao-Jun Li
• 刊名：ACS Catalysis
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：7
• 期：1
• 页码：510-519
• 全文大小：950K
• ISSN：2155-5435

文摘

Aryl halides are very useful electrophiles for synthesizing various substituted aromatic compounds via metal-catalyzed cross-coupling reactions. Because of the high cost associated with their synthesis and the stoichiometric halide waste produced when using aryl halide feedstocks, cheaper and more sustainable alternatives have been explored, such as phenols. However, phenols have a very reactive hydroxyl group and a C–O bond with high dissociation energy. To overcome such challenges, earlier studies focused on finding ways to reduce the energy of the C–O bond while removing the active proton by transforming phenols into phenol derivatives (e.g., sulfonates, esters, carbamates, ethers, and metal salts). A greater ambition is to directly cross-couple phenols with nucleophiles via C–O cleavage. In this Perspective, we briefly summarize efforts and accomplishments concerning the cross-coupling of phenol derivatives and phenols.