Synthesis of trifluoromethylthiolated azacalixarenepyridines from the Cu(ii)-mediated direct trifluoromethylthiolation reaction of arenes via reactive arylcopper(iii) intermediates†
Using azacalixarenepyridines and their high valent organocopper(II) and (III) complexes as probes, arene C–H bond trifluoromethylthiolation was investigated. While arylcopper(II) compounds appeared almost inert, arylcopper(III) compounds reacted efficiently with a nucleophilic trifluoromethylthiolating reagent. Under mild conditions, azacalixarenepyridines underwent the regioselective Cu(ClO4)2-mediated one-pot trifluoromethylthiolation reaction with Me4NSCF3 to afford low-rim functionalized macrocycles.
- This article is part of the themed collection: HOT articles in Organic Chemistry Frontiers in 2016