Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 27, Pages 5183-5191Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00684j
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Funding
- Carl-Zeiss Foundation
- Friedrich Schiller University Jena
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Thiazoles and benzothiazoles undergo regioselective C2-H chalcogenationviathe 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.
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