2026-04-29T20:04:07Zhttps://riubu.ubu.es/oai/request

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

Renedo Peña, Lorena 913 600 Álvarez Manuel, Estela 25 600 Solas Luera, Marta 542 600 0000-0002-0052-7270 Suárez Pantiga, Samuel 544 600 0000-0002-4249-7807 Fernández Rodríguez, Manuel A. 174 600 0000-0002-0120-5599 Sanz Díez, Roberto 531 600 0000-0003-2830-0892 2025-05-27T11:59:24Z 2025-05-27T11:59:24Z 2024-03 1615-4150 http://hdl.handle.net/10259/10501 10.1002/adsc.202301457 1615-4169 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. We gratefully acknowledge Ministerio de Ciencia e Innovación(PID2020-115789GB-C21/AEI/10.13039/501100011033), andJunta de Castilla y León and FEDER (BU028P23) for financialsupport. L.R. thanks Junta de Castilla y León (Consejería deEducación) and Fondo Social Europeo for a predoctoralcontract. S.S.-P. thanks Ministerio de Ciencia e Innovación and“NextGenerationEU”/PRTR EU for a Ramón y Cajal contract(RYC2021-031533-I). application/pdf eng Wiley Advanced Synthesus & Catalysis. 2024, V. 366, n. 9, p. 2079-2089 https://doi.org/10.1002/adsc.202301457 Atribución-NoComercial 4.0 Internacional http://creativecommons.org/licenses/by-nc/4.0/ info:eu-repo/semantics/openAccess Carbonyls Gold Homogeneous catalysis Indoles Oxidation Química Química orgánica Chemistry Chemistry, Organic Gold‐Catalyzed Tandem Oxidation‐Migration of 3‐Propargyl Indoles: Synthesis of α‐Indol‐3‐yl α,β‐Unsaturated Carbonyls info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Advanced Synthesis & Catalysis 366 9 2079 2089 THUMBNAIL Renedo-as&c_2024.pdf.jpg Renedo-as&c_2024.pdf.jpg IM Thumbnail image/jpeg 4922 https://riubu.ubu.es/bitstream/10259/10501/4/Renedo-as%26c_2024.pdf.jpg e938bdad109a48602236a1e664c1530d MD5 4 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/10501/3/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 3 CC-LICENSE license_rdf license_rdf application/rdf+xml; charset=utf-8 914 https://riubu.ubu.es/bitstream/10259/10501/2/license_rdf 24013099e9e6abb1575dc6ce0855efd5 MD5 2 ORIGINAL Renedo-as&c_2024.pdf Renedo-as&c_2024.pdf application/pdf 5901479 https://riubu.ubu.es/bitstream/10259/10501/1/Renedo-as%26c_2024.pdf 709eb4fec01729c4b87b601e0b2ee1b1 MD5 1 10259/10501 oai:riubu.ubu.es:10259/10501 2025-05-28 02:05:21.868 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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