期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 359, 期 14, 页码 2471-2480出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700270
关键词
difluoromethylthiolation; metal catalystfree conditions; perfluoroalkylthiolation; trifluoromethylthiolation
资金
- National Natural Science Foundation of China [21476116]
- Fundamental Research Funds for the Central Universities [30916011102]
- Natural Science Foundation of Jiangsu [BK20141394]
- Qing Lan and Six Talent Peaks in Jiangsu Province
- Priority Academic Program Development of Jiangsu Higher Education Institutions
- Center for Advanced Materials and Technology in Nanjing University of Science and Technology
A method for direct difluoromethylthiolation of Ar-H bonds is introduced. The stable and easy-to-handle HCF2SO2Na is reduced with (EtO)(2)P(O)H in the presence of TMSCl to generate HCF2S+ for the regioselective difluoromethylthiolation of aromatic compounds including indoles, pyrroles, and activated benzenes. This method is also applicable for the trifluoromethylthiolation with CF3SO2Na and the perfluoroalkylthiolation with RfSO2Na of arenes and heteroarenes. Reaction mechanisms associated with the metal-free electrophilic fluoroalkylthiolation reactions are also discussed.
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