RT info:eu-repo/semantics/article
T1 Gold‐Catalyzed Tandem Oxidation‐Migration of 3‐Propargyl Indoles: Synthesis of α‐Indol‐3‐yl α,β‐Unsaturated Carbonyls
A1 Renedo Peña, Lorena
A1 Álvarez Manuel, Estela
A1 Solas Luera, Marta
A1 Suárez Pantiga, Samuel
A1 Fernández Rodríguez, Manuel A.
A1 Sanz Díez, Roberto
K1 Carbonyls
K1 Gold
K1 Homogeneous catalysis
K1 Indoles
K1 Oxidation
K1 Química
K1 Chemistry
K1 Química orgánica
K1 Chemistry, Organic
AB α-Indol-3-yl α,β-unsaturated carbonyl compounds are synthesized from 3-propargyl indoles, obtained by direct propargylation of indoles, via a gold-catalyzed tandem oxidation-1,2-indole migration reaction in the presence of pyridine N-oxides. Fine-tuning of the catalyst and oxidant enables the reaction of 3-propargyl indoles bearing different substituents. The order of oxidation and indole migration is determined by the terminal or internal nature of the alkyne moiety. In addition, the process can be coupled with additional reactions, allowing an increase in molecular complexity or the design of more elaborated tandem reactions. In this sense, indole derivatives bearing an alkenyl substituent at the alkyne position evolve through a gold-catalyzed tandem oxidation-1,2-indole migration-Nazarov cyclization producing α-indolyl cyclopentenones.
PB Wiley
SN 1615-4150
YR 2024
FD 2024-03
LK http://hdl.handle.net/10259/10501
UL http://hdl.handle.net/10259/10501
LA eng
NO We gratefully acknowledge Ministerio de Ciencia e Innovación(PID2020-115789GB-C21/AEI/10.13039/501100011033), andJunta de Castilla y León and FEDER (BU028P23) for financialsupport. L.R. thanks Junta de Castilla y León (Consejería deEducación) and Fondo Social Europeo for a predoctoralcontract. 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 30-may-2025