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

2024-07-01T10:37:30Z urn:hdl:10259/9327 Catalyst‐ and Substrate‐Controlled Regiodivergent Synthesis of Carbazoles through Gold‐Catalyzed Cyclizations of Indole‐Functionalized Alkynols Solas Luera, Marta Muñoz Torres, Miguel Ángel Martínez Lara, Fernando Renedo Peña, Lorena Suarez Pantiga, Samuel Sanz Díez, Roberto Carbazoles Gold Homogeneous catalysis 1,2-migration Regioselectivity 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. 2024-07-01T10:37:30Z 2024-07-01T10:37:30Z 2023-09-29 info:eu-repo/semantics/article 2192-6506 http://hdl.handle.net/10259/9327 10.1002/cplu.202300382 2192-6506 eng ChemPlusChem. 2023, V. 88, n. 11 https://doi.org/10.1002/cplu.202300382 http://creativecommons.org/licenses/by-nc/4.0/ info:eu-repo/semantics/openAccess Atribución-NoComercial 4.0 Internacional Wiley