Copper-catalyzed remote C-H monofluoromethylation of 8-aminoquinolines with dimethyl phosphonate as reductant. Issue 40 (3rd October 2019)

• Record Type: Journal Article
• Authors: Han, Shuaijun; Wu, Qingsong; Mele, Lucas; Ding, Licheng; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Wu, Yangjie
• Is Part Of: Tetrahedron letters. Volume 60:Issue 40(2019)
• Publication Date: 2019-10-03
• Subjects: 8-Aminoquinolines -- Monofluoromethylation -- Copper -- C-H functionalization -- Dimethyl phosphonate; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151077
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A new approach to C5 ethoxycarbonylmonofluoromethylation of quinolines. Copper-catalyzed system was applied. This catalytic system features high-efficiency and synthetic convenience. The reaction proceeds under air. Abstract: A simple and efficient copper-catalyzed monofluoromethylation of 8-aminoquinolines with 2-bromo-2-fluoroacetate has been described with HPO(OMe)2 (dimethyl phosphonate) as reductant. The reaction tolerates a variety of quinoline amides and monofluoroalkyl bromides. Significant advantages of this protocol include synthetic convenience and high reaction efficiency.