The Cross‐Dehydrogenative Coupling Reaction of β‐Ketoesters with Quinoxalin‐2(1H)‐ones

• Published in: European journal of organic chemistry Vol. 2021; no. 14; pp. 2126 - 2130
• Main Authors: Zhang, Hong‐Yu, Yang, Zibing, Zhang, Huizhen, Han, Ya‐Ping, Zhao, Jiquan, Zhang, Yuecheng
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 15.04.2021; Wiley Subscription Services, Inc
• Subjects: Chemistry; Chemistry, Organic; Coupling; Cross-dehydrogenative coupling; Cu-catalysis; Dehydrogenation; Functional groups; Ionic mechanism; Physical Sciences; Quinoxalin-2(1H)-one; Science & Technology; β-Ketoesters; Cross-dehydrogenative coupling; 1,3-DICARBONYL COMPOUNDS; Quinoxalin-2(1H)-one; ARYLATION; OXIDATIVE-AMINATION; C-H FUNCTIONALIZATION; Ionic mechanism; POTENT; Cu-catalysis; QUINOXALINONES; QUINOXALIN-2(H)-ONES; beta-Ketoesters; METAL; BOND; EFFICIENT
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202100310

The cross‐dehydrogenative coupling (CDC) reaction of β‐ketoesters with quinoxalin‐2(1H)‐one derivatives has been successfully performed by using a readily available Cu salt as the catalyst in moderate to excellent yields under mild conditions. Owing to the characteristic of handy operation and good functional group tolerance, this protocol affords a convenient access to α‐quinoxalinone‐substituted β‐ketoesters. Preliminary mechanistic investigations show this transformation possibly underwent an unusual ionic pathway. A copper‐catalyzed CDC reaction of β‐ketoesters with quinoxalin‐2(1H)‐one derivatives has been developed, providing a series of α‐quinoxalinone‐substituted β‐ketoesters in moderate to excellent yields with good functional group tolerance. The preliminary mechanistic investigations indicate that this reaction possibly underwent an unusual ionic pathway.