Considering the high demand for methodologies involving the installation of fluorine atoms into molecules in the context of drug discovery, the biological relevance of sulfur and selenium compounds, and the relative lack of methods to incorporate chalcogen-containing fluoroalkyl moieties into molecules, we set out to develop a reagent system that would provide a means of accessing such scaffolds. Using a simple set of mild reaction conditions, with TMSCF3 as a difluorocarbene source, siladifluoromethyl selenoether [ArSeCF2TMS] and difluoromethyldichalcogenoacetal [(ArSe)2CF2 or (ArS)2CF2] products were obtained in moderate to excellent yields. Because selenols suffer from highly limited availability and a potent stench, a complementary method is presented, employing more convenient and easily-synthesized diselenides in lieu of selenols. The application of these novel synthons as chalcogeno-fluorofunctionalization reagents is also discussed.

Preparation of fluorinated selenium- and sulfur-containing compounds via reactions of selenols, diselenides, and disulfides with in situ-generated difluorocarbene and their potential uses for chalcogeno-fluorofunctionalization

2019 Fall National Meeting

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