Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 27, 2020
Previous Article Next Article

Selective C–H chalcogenation of thiazoles via thiazol-2-yl-phosphonium salts

Author affiliations

Abstract

Thiazoles and benzothiazoles undergo regioselective C2–H chalcogenation via the sequence of thiazole C2-functionalization with phosphines to produce phosphonium salts which in turn react with S- and Se-centered nucleophiles to give products of C2–H chalcogenation and allow for recovery of the starting phosphine. The atom economical sequence proceeds under mild conditions and features broad scope for both the nucleophiles (electron-rich, electron-poor, sterically hindered thiols) and the various substituted benzothiazoles. The access to the substituted medicinally relevant C2-thio benzothiazoles also enables stereoselectivity improvements in the modified Julia olefinations.

Graphical abstract: Selective C–H chalcogenation of thiazoles via thiazol-2-yl-phosphonium salts

Back to tab navigation

Supplementary files

Article information


Submitted
01 Apr 2020
Accepted
17 Jun 2020
First published
17 Jun 2020

Org. Biomol. Chem., 2020,18, 5183-5191
Article type
Paper

Selective C–H chalcogenation of thiazoles via thiazol-2-yl-phosphonium salts

Y. Zi, K. Wagner, F. Schömberg and I. Vilotijevic, Org. Biomol. Chem., 2020, 18, 5183
DOI: 10.1039/D0OB00684J

Social activity

Search articles by author

Spotlight

Advertisements