4.7 Article

Mn-Mediated Direct Regioselective C-H Trifluoromethylation of Imidazopyridines and Quinoxalines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 15, Pages 10599-10608

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c00621

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A simple and highly efficient strategy has been developed for direct C-H trifluoromethylation at C-3 of imidazopyridines and C-8 of quinoxalines using the readily available Langlois reagent through the KMnO4/AcOH system. This protocol exhibited a wide range of substrate compatibility and provided moderate-to-excellent yields of both products. It represents the first report of regioselective functionalization of quinoxalines at the C-8 position and mechanistic studies demonstrated a radical pathway.
A simple and highly efficient strategy has been developedfor directC-H trifluoromethylation at C-3 of imidazopyridines and C-8of quinoxalines with readily available Langlois reagent through KMnO4/AcOH system. This protocol showed broad substrate scope andafforded moderate-to-excellent yields of both products. It is thefirst report that the functionalization of quinoxalines occurred regioselectivelyat the C-8 position of quinoxalines. Mechanistic studies revealedthat reaction proceeded via radical pathway.

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