Accounting for Different Reactivities of Sulfinate and Thiosulfate Salts in Regioselective Azetidine Coupling via C–H Sulfenylation of Indoles

Abstract The regioselective incorporation of azetidines into heteroaromatic compounds is reported via a formal C–H sulfenylation reaction. While sodium sulfinate salts undergo C3 sulfenylation of electron-rich indoles only, the corresponding thiosulfate salts have proved to be more generally useful....

Full description

Saved in:
Bibliographic Details
Published in:Synlett 2018-02, Vol.29 (3), p.349-353
Main Authors: Al-Saedy, Muhannad A. E., Nassoy, Anne-Chloé M. A., Harrity, Joseph P. A.
Format: Article
Language:English
Subjects:
letter
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract The regioselective incorporation of azetidines into heteroaromatic compounds is reported via a formal C–H sulfenylation reaction. While sodium sulfinate salts undergo C3 sulfenylation of electron-rich indoles only, the corresponding thiosulfate salts have proved to be more generally useful. A mechanistic hypothesis for the different reactivities of sulfinate and thiosulfate salts is provided.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1591490