Abstract
Although oxygen, nitrogen, and carbon have been extensively studied as nucleophilic elements in the halocyclization of alkenes, sulfur-based nucleophiles are relatively unexplored. Herein, we investigated bromocyclization chemistry involving unsaturated thioesters, with a focus on their use as potential S-nucleophiles. We developed a bromocyclization method that uses alkenoic thioesters and N-bromoacetamide (NBA) to form cyclic bromosulfides. The resulting 5-exo products are labile and can be used in various nucleophilic substitution reactions.
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