2026-04-30T01:35:16Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/93272024-07-02T00:05:31Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Solas Luera, Marta 542 600 0000-0002-0052-7270 Muñoz Torres, Miguel Ángel 773 600 0000-0003-4372-9144 Martínez Lara, Fernando 345 600 0000-0002-2783-6778 Renedo Peña, Lorena 577faa28-7419-49ac-9b78-2a6cb4c9c7ca 600 Suarez Pantiga, Samuel 544 600 0000-0002-4249-7807 Sanz Díez, Roberto 531 600 0000-0003-2830-0892 2024-07-01T10:37:30Z 2024-07-01T10:37:30Z 2023-09-29 2192-6506 http://hdl.handle.net/10259/9327 10.1002/cplu.202300382 2192-6506 A wide variety of regioselectively substituted carbazole derivatives can be synthesized by the gold-catalyzed cyclization of alkynols bearing an indol-3-yl and an additional group at the homopropargylic positions. The regioselectivity of the process can be controlled by both the oxidation state of the gold catalyst and the electronic nature of the substituents of the alkynol moiety. The 1,2-alkyl migration in the spiroindoleninium intermediate, generated after indole attack to the activated alkyne, is favored with gold(I) complexes and for electron-rich aromatic substituents at the homopropargylic position, whereas the 1,2-alkenyl shift is preferred when using gold(III) salts and for alkyl or non-electron-rich aromatic groups. We gratefully acknowledge Ministerio de Ciencia e Innovación PID2020-115789GB−C21/AEI/10.13039/501100011033, and Junta de Castilla y León and FEDER (BU049P20) for financial support. M.A.M.-T., F.M.-L. and L.R. thank Consejería de Educación (Junta de Castilla y León) for predoctoral contracts. 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 ChemPlusChem. 2023, V. 88, n. 11 https://doi.org/10.1002/cplu.202300382 Atribución-NoComercial 4.0 Internacional http://creativecommons.org/licenses/by-nc/4.0/ info:eu-repo/semantics/openAccess Carbazoles Gold Homogeneous catalysis 1,2-migration Regioselectivity Química orgánica Chemistry, Organic Catalyst‐ and Substrate‐Controlled Regiodivergent Synthesis of Carbazoles through Gold‐Catalyzed Cyclizations of Indole‐Functionalized Alkynols info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion ChemPlusChem 88 11 THUMBNAIL Solas-cpc_2023.pdf.jpg Solas-cpc_2023.pdf.jpg IM Thumbnail image/jpeg 4785 https://riubu.ubu.es/bitstream/10259/9327/4/Solas-cpc_2023.pdf.jpg b564f71e128d2d0a68288117b603ff7e MD5 4 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/9327/3/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 3 CC-LICENSE license_rdf license_rdf application/rdf+xml; charset=utf-8 914 https://riubu.ubu.es/bitstream/10259/9327/2/license_rdf 24013099e9e6abb1575dc6ce0855efd5 MD5 2 ORIGINAL Solas-cpc_2023.pdf Solas-cpc_2023.pdf application/pdf 3190056 https://riubu.ubu.es/bitstream/10259/9327/1/Solas-cpc_2023.pdf a084173a665beb20b8cd736450836620 MD5 1 10259/9327 oai:riubu.ubu.es:10259/9327 2024-07-02 02:05:31.562 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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