School of Chemistry, Sun Yat-sen University, Guangzhou 510006, China.
J Am Chem Soc. 2022 Aug 31;144(34):15894-15902. doi: 10.1021/jacs.2c07529. Epub 2022 Aug 23.
Phenols are important organic molecules because they have found widespread applications in many fields. Herein, an efficient and practical approach to prepare phenols from benzoic acids via simple organic reagents at room temperature is reported. This approach is compatible with various functional groups and heterocycles and can be easily scaled up. To demonstrate its synthetic utility, bioactive molecules and unsymmetrical hexaarylbenzenes have been prepared by leveraging this transformation as strategic steps. Mechanistic investigations suggest that the key migration step involves a free carbocation instead of a radical intermediate. Considering the abundance of benzoic acids and the utility of phenols, it is anticipated that this method will find broad applications in organic synthesis.
酚类是重要的有机分子，因为它们在许多领域都有广泛的应用。在此，我们报道了一种在室温下通过简单有机试剂从苯甲酸制备酚类的高效实用方法。该方法适用于各种官能团和杂环，并且可以很容易地放大。为了证明其合成实用性，我们利用该转化作为关键步骤，制备了生物活性分子和不对称六芳基苯。机理研究表明，关键的迁移步骤涉及游离碳正离子而不是自由基中间体。考虑到苯甲酸的丰富性和酚类的实用性，预计该方法将在有机合成中得到广泛应用。
