Heteroaryl sulfoxides are an integral part of several bioactive molecules and pharmaceuticals. We have described a transition-metal-free route for the direct sulfinylation of 2-halobenzothiazoles and 2-halobenzimidazoles using β-sulfinyl esters as the source of the sulfenate ion in the presence of a Brønsted base such as LiOBu, and the corresponding heteroaryl sulfoxides were isolated in yields of 30 to 94%. Moreover, we hypothesized a plausible concerted nucleophilic aromatic substitution (cSAr) pathway for the direct incorporation of sulfinyl functionality into the 2-haloheteroarenes.
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