RT info:eu-repo/semantics/article
T1 Catalyst‐ and Substrate‐Controlled Regiodivergent Synthesis of Carbazoles through Gold‐Catalyzed Cyclizations of Indole‐Functionalized Alkynols
A1 Solas Luera, Marta
A1 Muñoz Torres, Miguel Ángel
A1 Martínez Lara, Fernando
A1 Renedo Peña, Lorena
A1 Suárez Pantiga, Samuel
A1 Sanz Díez, Roberto
K1 Carbazoles
K1 Gold
K1 Homogeneous catalysis
K1 1,2-migration
K1 Regioselectivity
K1 Química orgánica
K1 Chemistry, Organic
AB A wide variety of regioselectively substituted carbazole derivatives can be synthesized by the gold-catalyzed cyclization of alkynols bearing an indol-3-yl and an additional group at the homopropargylic positions. The regioselectivity of the process can be controlled by both the oxidation state of the gold catalyst and the electronic nature of the substituents of the alkynol moiety. The 1,2-alkyl migration in the spiroindoleninium intermediate, generated after indole attack to the activated alkyne, is favored with gold(I) complexes and for electron-rich aromatic substituents at the homopropargylic position, whereas the 1,2-alkenyl shift is preferred when using gold(III) salts and for alkyl or non-electron-rich aromatic groups.
PB Wiley
SN 2192-6506
YR 2023
FD 2023-09-29
LK http://hdl.handle.net/10259/9327
UL http://hdl.handle.net/10259/9327
LA eng
NO We gratefully acknowledge Ministerio de Ciencia e Innovación PID2020-115789GB−C21/AEI/10.13039/501100011033, and Junta de Castilla y León and FEDER (BU049P20) for financial support. M.A.M.-T., F.M.-L. and L.R. thank Consejería de Educación (Junta de Castilla y León) for predoctoral contracts. S.S.-P. thanks Ministerio de Ciencia e Innovación and “NextGenerationEU”/PRTR EU for a Ramón y Cajal contract (RYC2021-031533-I).
DS Repositorio Institucional de la Universidad de Burgos
RD 22-dic-2024