Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 22, Pages 3616-3626Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600693
Keywords
domino reactions; quinoline-2,4(1H,3H)-diones; radicals; sulfonylation; trifluoromethylation
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Funding
- National Natural Science Foundation of China [21402071]
- Kunming University of Science and Technology [KKSY201426046]
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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.
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