N-Heterocycles, such as pyrroles, are capable of being synthesized using titanium-based redox catalysis. Recently a titanium-catalyzed coupling reaction between N-sulfonyl-1,2,3-triazoles and alkynes was discovered, resulting in the unexpected synthesis of halovinyl sulfides. Vinyl sulfides are used in a wide variety of synthetic processes and are important precursors to a broad range of bioactive molecules. The current state-of-the-art method of synthesizing vinyl sulfides, transition metal catalyzed hydrothiolation, requires the use of less abundant and toxic noble metal catalysts such as rhodium and palladium. Furthermore, many hydrothiolation methods are not selective. Our research has demonstrated that vinyl sulfides can be synthesized using cheap and abundant titanium catalysts with high selectivity and moderate yields. Reactions with radical capture agents suggest that the synthesis proceeds via a radical mechanism. This new reaction pathway has shown promise as an alternative and complimentary method to currently used technology for the synthesis of vinyl sulfides. All products were characterized with 1H and 13C NMR spectroscopy after purification by column chromatography.

Titanium catalyzed coupling reactions of triazoles and alkynes: An unexpected synthesis of halovinyl sulfides

2019 Spring National Meeting

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