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 -nucleophiles. We developed a bromocyclization method that uses alkenoic thioesters and -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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Mechanistic Studies on Bromocyclization of Unsaturated Thioester by Density Functional Theory and Experiment.
J Org Chem
May 2024
Faculty of Pharmacy, Musashino University, 1-1-20 Shinmachi Nishitokyo, Tokyo 202-8585, Japan.
Using sulfur-containing nucleophiles in halocyclization has been underexplored notwithstanding their potential to generate novel -heterocycles and despite the extensive exploration of oxygen, nitrogen, and carbon nucleophiles. In this study, we focused on the bromocyclization of alkenoic thioesters with -bromoacetamide, which leads to the formation of cyclic bromosulfides. Investigation into the mechanistic pathways of these reactions revealed that the sulfur atom behaves as a nucleophile, leading to -acetylsulfonium intermediates.
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Faculty of Pharmacy, Musashino University, 1-1-20 Shinmachi Nishitokyo, Tokyo 202-8585, Japan.
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 -nucleophiles. We developed a bromocyclization method that uses alkenoic thioesters and -bromoacetamide (NBA) to form cyclic bromosulfides.
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