Synthesis of trifluoromethylthiolated azacalix[1]arene[3]pyridines from the Cu(ii)-mediated direct trifluoromethylthiolation reaction of arenes via reactive arylcopper(iii) intermediates

Literature Information

Publication Date 2016-05-20
DOI 10.1039/C6QO00161K
Impact Factor 5.281
Authors

Fei Wang, Liang Zhao, Jingsong You, Mei-Xiang Wang


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Abstract

Using azacalix[1]arene[3]pyridines 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, azacalix[1]arene[3]pyridines underwent the regioselective Cu(ClO4)2-mediated one-pot trifluoromethylthiolation reaction with Me4NSCF3 to afford low-rim functionalized macrocycles.

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