Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
J Am Chem Soc. 2011 Nov 9;133(44):17630-3. doi: 10.1021/ja208572v. Epub 2011 Oct 18.
A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product.
本文报道了一种硅醇导向的、钯催化的酚的 C-H 氧化反应，将其转化为邻苯二酚。该方法具有高度的位点选择性和通用性，不仅可以对电子中性的酚进行氧化，还可以对电子缺的酚进行氧化。该方法通过硅醇导向的乙酰氧基化作用进行，随后通过后续的酸催化环化反应形成环状硅保护的邻苯二酚。用 TBAF 对硅烷进行常规脱硅反应，即可得到邻苯二酚产物。
