Christian Doppler Laboratory for Entropy-Oriented Drug Design, Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria.
Boehringer-Ingelheim RCV, Doktor-Boehringer-Gasse 5-11, 1120 Vienna, Austria.
J Org Chem. 2022 Jan 7;87(1):606-612. doi: 10.1021/acs.joc.1c02616. Epub 2021 Dec 28.
Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.
在此,我们提出了一种通用的电化学方法,通过直接 C-H 功能化来获得不对称的 3,3-二取代的吲哚酮,其中吲哚酮片段表现为亲电试剂。这种反转策略不依赖于化学计量的氧化剂,在温和、环境友好的条件下进行。重要的是,它能够通过 C-O 对这些支架进行功能化,并且可以扩展到 C-C 甚至 C-N 键的形成。