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Published TCIMAIL newest issue No.198
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Trifluoromethylthiolating Agent Usable for Direct Dehydroxytrifluoromethylthiolation of Alcohols
Silver(I) trifluoromethanethiolate (1) has already been known as a trifluoromethylthiolating agent1,2) and is also applicable to direct dehydroxytrifluoromethylthiolation.3) 1 successfully gives trifluoromethanethiolate (2) by treatment with tetrabutylammonium iodide (TBAI) or potassium iodide.4) 2 is unstable and is known to decompose into carbonothioic difluoride (3) and fluoride anion. 3 reacts with alcohols to form an intermediate 4. Then, 4 reacts with 2 to afford the corresponding trifluoromethylthiolated product. The trifluoromethylthiolation by using 1 can be applied to alcohols with other functional groups and heterocyclic compounds, so that it is expected to be used in medicinal chemistry.
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References
- 1)Pd-Catalyzed Synthesis of Ar-SCF3 Compounds under Mild Conditions
- 2)Silver-Mediated Radical Aryltrifluoromethylthiolation of Activated Alkenes
- 3)Direct Dehydroxytrifluoromethylthiolation of Alcohols Using Silver(I) Trifluoromethanethiolate and Tetra-n-butylammonium Iodide
- 4)Preparation of Trifluoromethyl Aryl Sulfides Using Silver(I)Trifluoromethanethiolate and an Inorganic Iodide
