Copper-Mediated Oxidative Radical Addition/Cyclization Cascade: Synthesis of Trifluoromethylated and Sulfonated Quinoline-2,4(1H,3H)-diones

• Published in: Advanced synthesis & catalysis Vol. 358; no. 22; pp. 3616 - 3626
• Main Authors: Fu, Hong, Wang, Shi-Sheng, Li, Ya-Min
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 17.11.2016; Wiley
• Subjects: 3H)-diones; 4(1H; Carbon; Cascades; Chemistry; Chemistry, Applied; Chemistry, Organic; domino reactions; Imines; Physical Sciences; quinoline-2; quinoline-2,4(1H,3H)-diones; Radicals; Reagents; Science & Technology; Sodium; sulfonylation; Tolerances; Transformations; trifluoromethylation; ROOM-TEMPERATURE; SODIUM TRIFLUOROMETHANESULFINATE; radicals; sulfonylation; ONE-POT SYNTHESIS; N-ARYLACRYLAMIDES; EFFICIENT SYNTHESIS; PHOTOREDOX CATALYSIS; ACTIVATED ALKENES; domino reactions; CATALYZED TRIFLUOROMETHYLATION; trifluoromethylation; ARYL KETONES; quinoline-2,4(1H,3H)-diones; REDUCTIVE CYCLIZATION
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201600693

A copper‐mediated oxidative radical addition/cyclization cascade of o‐cyanoarylacrylamides with sodium trifluoromethanesulfonate (Langlois’ reagent) has been achieved. The reaction proceeds through radical addition, cyclization, and imine hydrolysis, in which the cyclization was accomplished by an intramolecular addition of the carbon radical to the nitrile. This transformation exhibits a wide substrate scope and good functional group tolerance, thus providing a highly efficient and practical access to a variety of trifluoromethylated quinoline‐2,4(1H,3H)‐diones. Furthermore, using other sulfinic acid sodium salts as sulfonylating agents, sulfonated quinolinediones were also obtained through a similar radical cascade.