Abstract
The perfluoroalkyl groups act as lipophilic electron-withdrawing groups, introducing additional unique properties in the molecules when compared to their non-fluorinated analogues. These properties are closely related to those of trifluoromethoxy (OCF3) and trifluoromethyl (CF3) groups. Initial search for conditions that could promote nucleophilic substitution showed, however, that bromides are completely inert and do not react under any conditions in which iodides showed reactivity. Due to the reduced nucleophilicity of the SCF3 anion, the coupling is considerably more difficult relative to non-fluorinated thiolate. However, to date, the direct synthesis of such significant compounds is unfortunately limited due to lack of safe, efficient, and general synthetic methods. There are few methods reported for the synthesis of vinyl trifluoromethyl thioethers with limited scope and moderate yields, the most recent one involving multistep procedures for the preparation of starting vinyl boronic acids and making use of expensive reagents in stoichiometric quantities.
Original language | English (US) |
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Pages (from-to) | 14043-14046 |
Number of pages | 4 |
Journal | Chemistry - A European Journal |
Volume | 19 |
Issue number | 42 |
DOIs | |
State | Published - Oct 11 2013 |
Externally published | Yes |
Keywords
- C-S bond formation
- Copper
- Thioethers
- Trifluoromethyl thiolation
- Vinyl iodide
ASJC Scopus subject areas
- General Chemistry
- Catalysis
- Organic Chemistry