State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai 201210, China.
Org Lett. 2020 Dec 18;22(24):9699-9705. doi: 10.1021/acs.orglett.0c03759. Epub 2020 Dec 9.
Dearomatization of indole derivatives offers a straightforward approach to access diverse indolines. To date, the corresponding dearomative transformations involving electron-deficient indoles are limited. Herein, we report a one-electron strategy for dearomatization of electron-deficient indoles via a photoredox-catalyzed hydroalkylation employing commercially available glycine derivatives as the hydrofunctionalization reagents. Followed by DBU-mediated lactamization, structurally appealing lactam-fused indolines are obtained in good to excellent yields with exclusive selectivity.
吲哚衍生物的去芳构化提供了一种直接的方法来获得各种吲哚啉。迄今为止，涉及缺电子吲哚的相应去芳构化转化是有限的。在此，我们报告了一种通过光氧化还原催化氢烷基化反应，使用商业上可用的甘氨酸衍生物作为氢官能化试剂，来实现缺电子吲哚去芳构化的单电子策略。随后通过 DBU 介导的内酰胺化反应，可以以良好到优异的收率和优异的选择性得到结构吸引人的内酰胺稠合吲哚啉。
