Open AccessStraightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides
Author(s) -
Pierre Thilmany,
Alejandro GuarnieriIbáñez,
Clément Jacob,
Jérôme Lacour,
Gwilherm Evano
Publication year - 2021
Publication title -
acs organic and inorganic au
Language(s) - English
Resource type - Journals
ISSN - 2694-247X
DOI - 10.1021/acsorginorgau.1c00021
Subject(s) - intramolecular force , catalysis , chemistry , combinatorial chemistry , computer science , stereochemistry , organic chemistry
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.