Photoinitiated Deaminative Alkylation of Quinoxalin‐2(1H)‐ones via Electron Catalysis. Issue 6 (8th March 2023)

• Record Type: Journal Article
• Authors: Deng, Yangling; Cheng, Xiya; Tan, Heping; He, Yuxuan; Zhang, Changmei; Qiu, Guanyinsheng; Zheng, Danqing
• Is Part Of: Advanced synthesis & catalysis. Volume 365:Issue 6(2023)
• Page Start: 865
• Page End: 870
• Publication Date: 2023-03-08
• Subjects: deaminative alkylation -- quinoxalin-2(1H)-one -- Katritzky salt -- electron catalysis -- radical cascade; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202300035
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract : A visible‐light initiated deaminative C3 alkylation of quinoxalin‐2(1 H )‐ones with Katritzky salts is reported. This radical process provides an approach to a range of C3 alkylated quinoxalin‐2(1 H )‐one derivatives in 40–96% yields under metal‐ and external photocatalyst‐free conditions. The reaction is enabled by the deprotonation of acidic aminyl radical intermediates to generate the corresponding radical anions, which act as single electron transfer reducing reagents to sustain the radical chain. The late‐stage functionalization of drug‐based amines further demonstrates the value of this approach.