Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides

An original and straightforward entry to polysubstituted indenes from readily available ynamides is reported. Upon reaction with a N-heterocyclic carbene–gold complex under mild conditions, activated keteniminium ions are generated whose unique electrophilicity triggers a [1,5]-hydride shift and a s...

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Veröffentlicht in:ACS Organic & Inorganic Au 2022-02, Vol.2 (1), p.53-58
Hauptverfasser: Thilmany, Pierre, Guarnieri-Ibáñez, Alejandro, Jacob, Clément, Lacour, Jérôme, Evano, Gwilherm
Format: Artikel
Sprache:eng
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Zusammenfassung:An original and straightforward entry to polysubstituted indenes from readily available ynamides is reported. Upon reaction with a N-heterocyclic carbene–gold complex under mild conditions, activated keteniminium ions are generated whose unique electrophilicity triggers a [1,5]-hydride shift and a subsequent cyclization. The presence of an endocyclic enamide in the densely functionalized resulting indenes was shown to be especially useful and versatile, offering a range of opportunities for their further postfunctionalization.
ISSN:2694-247X
2694-247X
DOI:10.1021/acsorginorgau.1c00021