2026-08-29T14:44:11Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/39142021-11-10T09:38:24Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Regioselective synthesis of elusive 4,9-Dihydro-1H-Carbazoles by gold-catalyzed cycloisomerization of 3-Allenylmethylindoles Álvarez Manuel, Estela García García, Patricia Fernández Rodríguez, Manuel A. Sanz Díez, Roberto A general and efficient synthesis of 4,9-dihydro- 1H-carbazoles from 3-allenylmethylindoles is reported. The process, catalyzed by a cationic gold(I) complex, involves a formal C2−H bond activation of the indole unit by reaction with the allene. The nature of the substituents at the allylic and terminal positions of the allene moiety has a crucial effect on the regioselectivity of the cyclization, which is also influenced by the catalyst and the solvent employed. Moreover, some evidence of the contribution of different reaction routes is provided, which led us to propose a plausible multipathway mechanism consistent with all of the results described. 2016-01-27T10:11:46Z 2016-01-27T10:11:46Z 2016-01-27T10:11:46Z 2013-09 info:eu-repo/semantics/article 0022-3263 http://hdl.handle.net/10259/3914 10.1021/jo401388b eng Journal of organic chemistry. 2013, V. 78, n. 19, p. 9758–9771 http://dx.doi.org/10.1021/jo401388b info:eu-repo/grantAgreement/MICINN-FEDER/CTQ2010-15358 info:eu-repo/grantAgreement/MICINN-FEDER/CTQ2009-09949/BQU info:eu-repo/semantics/openAccess American Chemical Society