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

par Thilmany, Pierre ;Guarnieri-Ibáñez, Alejandro;Jacob, Clément ;Lacour, Jérome;Evano, Gwilherm
Référence ACS Organic & Inorganic Au, 2, page (53-58)
Publication Publié, 2022-02-01

Article révisé par les pairs

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Résumé :

An original and straightforward entry to polysubstituted indenes from readily available ynamides is reported. Upon reaction with a NHC-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 post-functionalization.