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Selective C-H Chalcogenation of Thiazoles via Thiazol-2-yl-phosphonium Salts.pdf (548.06 kB)
Selective C-H Chalcogenation of Thiazoles via Thiazol-2-yl-phosphonium Salts
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submitted on 17.04.2020 and posted on 20.04.2020by You Zi, Konrad Wagner, Fritz Schömberg, Ivan Vilotijevic
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.