RT info:eu-repo/semantics/article
T1 Gold-Catalyzed Synthesis of 1-(Indol-3-yl)carbazoles: Selective 1,2-Alkyl vs 1,2-Vinyl Migration
A1 Suárez, Anisley
A1 Suarez Pantiga, Samuel
A1 Nieto Faza, Olalla .
A1 Sanz Díez, Roberto
K1 Química orgánica
K1 Chemistry, Organic
AB 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.
PB American Chemical Society
SN 1523-7060
YR 2017
FD 2017-10
LK http://hdl.handle.net/10259/4926
UL http://hdl.handle.net/10259/4926
LA eng
NO Junta de Castilla y León and FEDER(BU076U16) and Ministerio de Economíay Competitividad(MINECO) (CTQ2016-75023-C2-1-P and CTQ2016-75023-C2-2-P)
DS Repositorio Institucional de la Universidad de Burgos
RD 25-abr-2024