2026-06-19T23:01:17Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/49262021-11-10T09:38:25Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
Gold-Catalyzed Synthesis of 1-(Indol-3-yl)carbazoles: Selective 1,2-Alkyl vs 1,2-Vinyl Migration
Suárez, Anisley
Suarez Pantiga, Samuel
Nieto Faza, Olalla .
Sanz Díez, Roberto
Química orgánica
Chemistry, Organic
Gold(III)-catalyzed cycloisomerization of α-bis(indol-3-yl)methyl alkynols selectively affords 1-(indol-3-yl)carbazoles, in a transformation that takes place through a selective 1,2-alkyl vs 1,2-vinyl migration step in the vinyl-gold intermediate generated from the initial 5-endo-spirocyclization. The reaction proceeds well with either tertiary or secondary starting alkynols as well as with a wide variety of alkyne substituents. The key role of the other indol-3-yl substituent for the unexpected selectivity in the 1,2 rearrangement has also been supported by DFT calculations that reveal a low barrier, two-step mechanism in the alkyl migration path where the second indole significantly stabilizes a carbocationic intermediate.
Junta de Castilla y León and FEDER
(BU076U16) and Ministerio de Economía
y Competitividad
(MINECO) (CTQ2016-75023-C2-1-P and CTQ2016-75023-
C2-2-P)
2018-09-07T10:56:59Z
2018-10-06T02:45:06Z
2017-10
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
1523-7060
http://hdl.handle.net/10259/4926
10.1021/acs.orglett.7b02303
eng
Organic Letters. 2018, V. 19, n. 19, p. 5074–5077
https://doi.org/10.1021/acs.orglett.7b02303
info:eu-repo/grantAgreement/JCyL/BU076U16
info:eu-repo/grantAgreement/MINECO/CTQ2016-75023-C2-1-P
info:eu-repo/grantAgreement/MINECO/CTQ2016-75023-C2-2-P
info:eu-repo/semantics/openAccess
application/pdf
American Chemical Society