Electrochemical decarboxylative C3 alkylation of quinoxalin-2(1 H)-ones with N-hydroxyphthalimide esters

Kaikai Niu; Lingyun Song; Yanke Hao; Yuxiu Liu; Qingmin Wang

doi:10.1039/d0cc05391k

Electrochemical decarboxylative C3 alkylation of quinoxalin-2(1 H)-ones with N-hydroxyphthalimide esters

Chem Commun (Camb). 2020 Oct 1;56(78):11673-11676. doi: 10.1039/d0cc05391k.

Authors

Kaikai Niu¹, Lingyun Song¹, Yanke Hao¹, Yuxiu Liu¹, Qingmin Wang²

Affiliations

¹ State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China. wangqm@nankai.edu.cn.
² State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China. wangqm@nankai.edu.cn and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300071, People's Republic of China.

PMID: 33000793
DOI: 10.1039/d0cc05391k

Abstract

We have developed a protocol for electrochemical decarboxylative C3 alkylation of a wide range of quinoxalin-2(1H)-ones under metal- and additive-free conditions. N-Hydroxyphthalimide esters derived from chain, cyclic, primary, secondary, and tertiary carboxylic acids with a broad scope proved to be suitable substrates. This operationally simple protocol performed in an undivided cell under constant-current conditions is suitable for late-stage functionalization of quinoxalin-2(1H)-ones. The reactions can even be carried out with a 3 V battery as a power source, which demonstrates that organic electrosynthesis can be accomplished without the need for specialized equipment.