Regioselective ortho-trifluoromethylthiolation of 2-arylbenzo[d]thiazole via tandem substrate-assisted C–H iodination and trifluoromethylthiolation?

Organic & Biomolecular Chemistry Pub Date: 2016-02-04 DOI: 10.1039/C6OB00005C

Abstract

A mild and efficient tandem benzo[d]thiazole directed C–H iodination and trifluoromethylthiolation for the synthesis of ortho-trifluoromethylthiolated 2-arylbenzo[d]thiazoles have been developed using AgSCF3 as a coupling partner. The reaction exhibits a diverse array of functional group tolerance giving the desired products in good to excellent yields. Regioselective trifluoromethylthiolation was observed at the less sterically hindered site when the phenyl ring of the substrate possesses a methyl group at its meta position.

Graphical abstract: Regioselective ortho-trifluoromethylthiolation of 2-arylbenzo[d]thiazole via tandem substrate-assisted C–H iodination and trifluoromethylthiolation
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