2024-03-28T19:07:42Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/39142021-11-10T09:38:24Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
00925njm 22002777a 4500
dc
Álvarez Manuel, Estela
author
García García, Patricia
author
Fernández Rodríguez, Manuel A.
author
Sanz Díez, Roberto
author
2013-09
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.
0022-3263
http://hdl.handle.net/10259/3914
10.1021/jo401388b
Regioselective synthesis of elusive 4,9-Dihydro-1H-Carbazoles by gold-catalyzed cycloisomerization of 3-Allenylmethylindoles