钯催化的双齿辅助的苄位 C-H 键的氧化乙酰化反应。

Palladium-catalyzed oxidative acetoxylation of benzylic C-H bond using bidentate auxiliary.

机构信息

ZJU-NHU United R&D Center, Department of Chemistry, Zhejiang University , Hangzhou 310027, China.

出版信息

J Org Chem. 2013 Nov 1;78(21):10821-31. doi: 10.1021/jo401830k. Epub 2013 Oct 24.

Abstract

Pd(OAc)2-catalyzed oxidative acetoxylation of benzylic C-H bonds utilizing a bidentate system has been explored. A variety of picolinoyl- or quinoline-2-carbonyl-protected toluidine derivatives react with PhI(OAc)2 in the presence of Pd(OAc)2 to afford the acetoxylated products in synthetically useful yields. A broad of functionalities, such as CH3, F, Cl, Br, I, COCH3, CO2Et, SO2CH3, and NO2, were tolerated. This transformation provides easy access to 2-hydroxymethylaniline derivatives.

摘要

Pd(OAc)2 催化的利用双齿体系的苄位 C-H 键的氧化乙酰化反应已经被探索。各种吡啶甲酰基或喹啉-2-羰基保护的甲苯胺衍生物在 Pd(OAc)2 的存在下与 PhI(OAc)2 反应，以合成上有用的产率得到乙酰化产物。广泛的官能团，如 CH3、F、Cl、Br、I、COCH3、CO2Et、SO2CH3 和 NO2，都可以耐受。这种转化提供了易于获得 2-羟甲基苯胺衍生物的途径。