Brønsted acid-mediated thiazole synthesis from sulfoxonium ylides

A Brønsted acid-mediated insertion of thioureas/thioamides into sulfoxonium ylides to synthesise 40 thiazoles (34-95% yields) under mild, metal-free conditions is described. This process is scalable, substrate-tolerant (including both α-substituted and heterocyclic ylides/groups) and was successfull...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2024-10, Vol.6 (85), p.1241-1244
Hauptverfasser: Smy, Joe L, Ifill, Roxanne, Hassell-Hart, Storm
Format: Artikel
Sprache:eng
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Zusammenfassung:A Brønsted acid-mediated insertion of thioureas/thioamides into sulfoxonium ylides to synthesise 40 thiazoles (34-95% yields) under mild, metal-free conditions is described. This process is scalable, substrate-tolerant (including both α-substituted and heterocyclic ylides/groups) and was successfully applied to the late-stage functionalisation of the complex chemical probe molecule (+)-JQ1. A Brønsted acid-mediated insertion of thioureas/thioamides into sulfoxonium ylides to synthesise 40 thiazoles (34-95% yields) under mild, metal-free conditions is described.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc03905j