Issue 7, 2016

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
16 apr 2016
Accepted
19 máj 2016
First published
20 máj 2016

Org. Chem. Front., 2016,3, 880-886

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

F. Wang, L. Zhao, J. You and M. Wang, Org. Chem. Front., 2016, 3, 880 DOI: 10.1039/C6QO00161K

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