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

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 AgSCF 3 as a coupling partner. The reaction exhibits a diverse array of functional group toler...

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Published inOrganic & biomolecular chemistry Vol. 14; no. 10; pp. 2924 - 2929
Main Authors Luo, Puying, Ding, Qiuping, Ping, Yuanyuan, Hu, Jianan
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BORONIC ACIDS
MILD
POTENT
IODONIUM YLIDE
ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION
HYPERVALENT IODINE REAGENT
ARYL
COPPER-CATALYZED TRIFLUOROMETHYLTHIOLATION
ENANTIOSELECTIVE TRIFLUOROMETHYLTHIOLATION
CYCLIZATION
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Summary: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 AgSCF 3 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/C6OB00005C