Aromatic carbon-sulfur bonds are highly important structural motifs, which appear in natural products, drugs, as well as in ligands for asymmetric catalysis. Furthermore, molecules containing an aromatic C-S bond are very common in the field of materials science. Usually, the C-S bond is formed by reductive coupling reactions employing transition metal catalysts. Although these reactions are well established, they are limited to precursor molecules equipped with leaving groups, which results in a poor atomic economy and tedious multi-step sequences. In order to overcome this disadvantages, a direct C-H sulfenylation of arenes is highly desirable. Molybdenum pentachloride is a readily available bulk chemical, which has shown an impressive reactivity towards disulfides in previous studies on the formation of thianthrenes. Recently, we were able to broaden the product range of the MoV mediated sulfenylation by employing this reaction in the synthesis of mixed sulfides and sulfur heterocycles. These transformations open up much more efficient and straight-forward pathways for the access to those compound classes.

Access to sulfides and sulfur heterocycles by oxidative C-S bond formation using MoV reagents

256th National Meeting (2018)

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