期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 26, 页码 7648-7652出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502113
关键词
copper; diazo compounds; fluorine; heterocycles; synthetic methods
资金
- National Basic Research Program of China [2012CB821600]
- National Natural Science Foundation of China [21172245/21172244/21372247/21421002]
- Syngenta PhD fellowship
- sioc
An efficient copper-promoted difluoromethylthiolation of aryl and heteroaryl diazonium salts is described. The reaction is conducted under mild reaction conditions and various functional groups were compatible. In addition, reactions of heteroaryl diazonium salts such as pyridyl, quinolinyl, benzothiazolyl, thiophenyl, carbazolyl, and pyrazolyl diazonium salts occurred smoothly to afford the medicinally important difluoromethylthiolated heteroarenes. Furthermore, a more practical one-pot direct diazotization and difluoromethylthiolation protocol was developed, and it converts the aniline derivatives into difluoromethylthiolated arenes. The utility of the method is demonstrated by difluoromethylthiolation of a number of natural products and drug molecules.
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