The State Key Laboratory of Applied Organic Chemistry, Lanzhou University, 222 Tianshui Road, Lanzhou, 730000, P. R. China.
Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. West, Montreal, Quebec, H3A 0B8, Canada.
Angew Chem Int Ed Engl. 2021 Feb 19;60(8):4043-4048. doi: 10.1002/anie.202010845. Epub 2020 Dec 27.
Phenols are common precursors and core structures of a variety of industrial chemicals ranging from pharmaceuticals to polymers. However, the synthesis of site-specifically substituted phenols is challenging, and thus the development of new methods for this purpose would be highly desirable. Reported here is a protocol for palladium-catalyzed ortho-selective alkylation reactions of phenols with primary alcohols by a dearomatization-rearomatization strategy, with water as the sole by-product. Various substituted phenols and primary alcohols were compatible with the standard reaction conditions. The detailed mechanism of this transformation was also investigated.
酚类是各种工业化学品（从药物到聚合物）的常见前体和核心结构。然而，具有特定取代基的酚类的合成具有挑战性，因此非常需要为此目的开发新的方法。本文报道了一种通过去芳构化-再芳构化策略，使用钯催化酚与伯醇的邻位选择性烷基化反应的方案，以水为唯一的副产物。各种取代的酚和伯醇都与标准反应条件兼容。还研究了这种转化的详细机理。
