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Issue 10, 2016
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Regioselective ortho-trifluoromethylthiolation of 2-arylbenzo[d]thiazole via tandem substrate-assisted C–H iodination and trifluoromethylthiolation

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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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Article information


Submitted
03 Jan 2016
Accepted
03 Feb 2016
First published
04 Feb 2016

Org. Biomol. Chem., 2016,14, 2924-2929
Article type
Paper

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

P. Luo, Q. Ding, Y. Ping and J. Hu, Org. Biomol. Chem., 2016, 14, 2924
DOI: 10.1039/C6OB00005C

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