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...

Full description

Saved in:
Bibliographic Details
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
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02147