Regioselective C–H Sulfanylation of Aryl Sulfoxides by Means of Pummerer-Type Activation

A regioselective C–H sulfanylation of aryl sulfoxides with alkyl aryl sulfides in the presence of acid anhydride was developed, which resulted in the formation of 1,4-disulfanylarenes after dealkylation of initially formed sulfonium salts. The reaction began with Pummerer-type activation of aryl sul...

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Published in:Organic letters 2017-09, Vol.19 (17), p.4552-4555
Main Authors: Kawashima, Hitomi, Yanagi, Tomoyuki, Wu, Chien-Chi, Nogi, Keisuke, Yorimitsu, Hideki
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cited_by cdi_FETCH-LOGICAL-a500t-c664e85809411f654893f34ac5342d6dc9b68fc658573d0b95ad131d9c600af13
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container_end_page 4555
container_issue 17
container_start_page 4552
container_title Organic letters
container_volume 19
creator Kawashima, Hitomi
Yanagi, Tomoyuki
Wu, Chien-Chi
Nogi, Keisuke
Yorimitsu, Hideki
description A regioselective C–H sulfanylation of aryl sulfoxides with alkyl aryl sulfides in the presence of acid anhydride was developed, which resulted in the formation of 1,4-disulfanylarenes after dealkylation of initially formed sulfonium salts. The reaction began with Pummerer-type activation of aryl sulfoxides followed by nucleophilic attack of alkyl aryl sulfides. The nucleophilic attack occurred exclusively at the para positions, or at specific positions in case the para position was not available, under perfect control by the dominating sulfoxide directors regardless of any other substituents. The initially formed aryl sulfonium salts were isolable and usefully served as aryl halide surrogates for palladium-catalyzed arylation with sodium tetraarylborates.
doi_str_mv 10.1021/acs.orglett.7b02147
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title Regioselective C–H Sulfanylation of Aryl Sulfoxides by Means of Pummerer-Type Activation
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