文献类型：期刊文献

英文题名：Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant

作者：He, Yun-Gang[1];Huang, Yong-Kang[1];Fan, Qi-Qi[1];Zheng, Bo[1];Luo, Yong-Qiang[1];Zhu, Xing-Liang[1];Shi, Xiao-Xin[1]

机构：[1]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm, Minist Educ, Shanghai 200237, Peoples R China

年份：2021

卷号：11

期号：47

起止页码：29702

外文期刊名：RSC ADVANCES

收录：;EI(收录号：20214110990978);WOS:【SCI-EXPANDED(收录号:WOS:000702237900053)】；

基金：We thank the National Natural Science Foundation of China (No. 20972048) for the financial support of this work.

语种：英文

外文关键词：Oxidants - Regioselectivity - Metabolites - Copper compounds - Oxidation - Catalysis

摘要：A mild, efficient and eco-friendly method for the oxidation of 1-Bn-DHIQs to 1-Bz-DHIQs without concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs is very important for the syntheses of 1-Bz-DHIQ alkaloids and analogues. In this article, we developed a novel Cu(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp(3))-H bonds adjacent to the C-1 positions of various 1-Bn-DHIQs. It was observed that when 0.2 equiv. of Cu(OAc)(2)center dot 2H(2)O was used as the catalyst, 3.0 equiv. of AcOH was used as the additive and air (O-2) was used as a clean oxidant, various 1-Bn-DHIQs could be efficiently oxidized to corresponding 1-Bz-DHIQs at 25 degrees C in DMSO. Especially, almost no concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs was observed during the above reaction. In addition, this method was successfully applied in the first total synthesis of the alkaloid canelillinoxine.