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oai:riubu.ubu.es:10259/105012025-05-28T00:05:21Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Renedo Peña, Lorena Álvarez Manuel, Estela Solas Luera, Marta Suárez Pantiga, Samuel Fernández Rodríguez, Manuel A. Sanz Díez, Roberto Carbonyls Gold Homogeneous catalysis Indoles Oxidation α-Indol-3-yl α,β-unsaturated carbonyl compounds are synthesized from 3-propargyl indoles, obtained by direct propargylation of indoles, via a gold-catalyzed tandem oxidation-1,2-indole migration reaction in the presence of pyridine N-oxides. Fine-tuning of the catalyst and oxidant enables the reaction of 3-propargyl indoles bearing different substituents. The order of oxidation and indole migration is determined by the terminal or internal nature of the alkyne moiety. In addition, the process can be coupled with additional reactions, allowing an increase in molecular complexity or the design of more elaborated tandem reactions. In this sense, indole derivatives bearing an alkenyl substituent at the alkyne position evolve through a gold-catalyzed tandem oxidation-1,2-indole migration-Nazarov cyclization producing α-indolyl cyclopentenones. 2025-05-27 2025-05-27 2024-03 info:eu-repo/semantics/article 1615-4150 http://hdl.handle.net/10259/10501 10.1002/adsc.202301457 1615-4169 eng Advanced Synthesus & Catalysis. 2024, V. 366, n. 9, p. 2079-2089 https://doi.org/10.1002/adsc.202301457 http://creativecommons.org/licenses/by-nc/4.0/ info:eu-repo/semantics/openAccess Atribución-NoComercial 4.0 Internacional Wiley