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Publication 226  

  1. Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides
    Pierre Thilmany, Alejandro Guarnieri-Ibáñez, Clément Jacob, Jérôme Lacour, Gwilherm Evano
    ACS Org. Inorg. Au 2022, 2, 53-58

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.

DOI: 10.1021/acsorginorgau.1c00021 

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