%0 Journal Article
%A Luna Costales, Amparo
%A Herrera García, Fernando
%A Murillo Lizcano, Alejandro
%A Higuera Velasco, Sheila
%A Fernández López, Israel
%A Almendros Requena, Pedro
%T AgNO3·SiO2: Convenient AgNPs source for the sustainable hydrofunctionalization of allenyl-indoles using heterogeneous catalysis
%D 2020
%@ 0021-9517
%U https://hdl.handle.net/20.500.14352/115793
%X Supported silver nitrate in silica gel has been demonstrated as an excellent heterogeneous catalytic system for the selective hydroarylation of indole-tethered allenes, with a selectivity reversal in comparison with homogeneous gold catalysis. In this way, the controlled preparation of 1,2-disubstituted-9H-carbazoles, 1,2-disubstituted-4,9-dihydro-1H-carbazoles, and 2,4-disubstituted-spiro[cyclopentane-1,3′-indol]-3-enes has been accomplished. Control experiments supported by Density Functional Theory calculations strongly suggest that indole-tethered allenes react through a 5-endo-dig-carbometallation/rearrangement sequence, which contrasts to the previously reported 6-endo-dig-carbometallation pathway promoted by [Au(I)]-catalysts in related systems.
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