Electrochemical C–H functionalization to synthesize 3-hydroxyalkylquinoxalin-2(1H)-ones via quinoxalin-2(1H)-ones and aldehydes. Issue 21 (26th September 2022)

• Record Type: Journal Article
• Authors: Liu, Han-Fu; He, Mu-Xue; Tang, Hai-Tao
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 21(2022)
• Page Start: 5955
• Page End: 5961
• Publication Date: 2022-09-26
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01281b
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : We reported an electrocatalytic direct C3-hydroxyalkylation of quinoxalin-2(1 H )-ones to construct 3-hydroxyalkylquinoxalin-2(1 H )-one derivatives, which uses unprotected quinoxalin-2(1 H )-ones and aliphatic aldehydes as substrates. Abstract : Direct C3-functionalization of quinoxalin-2(1 H )-ones is a convenient way to develop new and sustainable strategies, which are important for natural product and drug modification. Herein, we report an electrocatalytic C–H activation method, which synthesized 3-hydroxyalkylquinoxalin-2(1 H )-ones via a radical pathway using unprotected quinoxalin-2(1 H )-ones and aliphatic aldehydes as the substrates. This electrolysis strategy avoids the use of stoichiometric oxidants and heavy metal catalysts. Further scale-up studies in electrochemical continuous flow reactors have demonstrated the potential application value.