期刊
JOURNAL OF FLUORINE CHEMISTRY
卷 132, 期 12, 页码 1241-1246出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2011.07.008
关键词
Trifluoromethylation; CF(3)l solution; Trifluoromethyl sulfides; Steam-distillation
资金
- Hungarian Scientific Research Foundation (OTKA) [K 062191]
- European Union
- European Social Fund [TAMOP_4.2.1./B-09/1/KMR-2010-0003]
- Sanofi-aventis/Chinoin
Various aryl-, heteroaryl-, and alkyl mercaptanes (RSH, 1a-r) were treated with a slight excess of NaH suspended in DMF to make the appropriate sodium thiolates (RSNa), which then reacted with 1.3 equivalent of CF3I at room temperature for overnight to afford the appropriate trifluoromethyl sulfides (CF3SR, 2) in fair to good yields. The radical chain alkylation reaction was effective without the use of UV irradiation with all but three substrates (thiosalicylic acid, 1k; 2-mercaptobenzimidazole, 1q; and 3-mercaptopropionic acid, 1r). Steam-distillation was found as an effective and easy to upscale means for the isolation of these volatile and water immiscible sulfides. The CF3I reagent gas was conveniently weighed and delivered to the reaction mixture by the balloon technique or as a preliminary made stock solution in DMF or DMSO. The sulfides 2 obtained here were assayed by GC and characterized by H-1, C-13, F-19 NMR and MS spectroscopy. (C) 2011 Elsevier B.V. All rights reserved.
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