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钴催化的酚类化合物的 C-H 乙酰化反应:邻苯二酚衍生物的合成。

Cobalt-Catalyzed C-H Acetoxylation of Phenols with Removable Monodentate Directing Groups: Access to Pyrocatechol Derivatives.

机构信息

School of Chemistry and Chemical Engineering, Laboratory of Natural Medicine Research and Development in Wuling Mountain, Yangtze Normal University, Chongqing 408100, China.

Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000 Gent, Belgium.

出版信息

Org Lett. 2020 Mar 6;22(5):1966-1971. doi: 10.1021/acs.orglett.0c00312. Epub 2020 Feb 19.

Abstract

An efficient cobalt-catalyzed C-H acetoxylation of phenols has been developed by using PIDA (phenyliodine diacetate) as a sole acetoxy source to synthesize pyrocatechol derivatives for the first time. The key feature of this method is the use of earth-abundant metal cobalt as the green and inexpensive catalyst for the acetoxylation of C(sp)-H bonds under neutral reaction conditions. Furthermore, the gram-scale reaction and late-stage functionalization demonstrated the usefulness of this method.

摘要

发展了一种高效的钴催化酚类 C-H 乙酰化反应,首次使用 PIDA(苯碘酰二乙酸酯)作为唯一的乙酰氧基源来合成邻苯二酚衍生物。该方法的关键特点是使用丰富的金属钴作为绿色、廉价的催化剂,在中性反应条件下实现 C(sp)-H 键的乙酰化。此外,克级反应和后期官能团化实验证明了该方法的实用性。

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