2024-03-29T08:12:05Zhttps://riubu.ubu.es/oai/requestoai: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
Química orgánica
Chemistry, Organic
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.
MICINN and FEDER (CTQ2010-15358 and CTQ2009-09949/BQU) for financial support. E.A. thanks MEC for an FPU predoctoral fellowship. P.G.-G. and M.A.F.-R. thank MICINN for "Juan de la Cierva" and "Ramon y Cajal" contracts
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher.
2016-01-27T10:11:46Z
2016-01-27T10:11:46Z
2013-09
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
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
application/pdf
American Chemical Society