2026-06-18T00:56:56Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/74162023-03-28T08:17:24Zcom_10259_3592com_10259_3591com_10259.4_106com_10259_2604com_10259_3593com_10259_5086col_10259_3930col_10259_3594
2023-02-07T13:34:36Z
urn:hdl:10259/7416
“Back‐to‐Front” Indole and Carbazole Synthesis from N,N‐Bis‐(2‐bromoallyl)amines by Combining Carbolithiation Reactions with Gold‐Catalysis
Muñoz Torres, Miguel Ángel
Martínez Lara, Fernando
Solas Luera, Marta
Suarez Pantiga, Samuel
Sanz Díez, Roberto
Carbolithiation
Gold
Homogeneous catalysis
Nitrogen heterocycles
Organolithiums
The combination of organolithium chemistry with gold catalysis has enabled the development of a
synthetic strategy for accessing polysubstituted indoles and carbazoles from readily available starting materials.
This method is based on a “back-to-front” approach from ketopyrroles, generated by intramolecular
carbolithiation of N,N-bis-(2-lithioallyl)amines that evolve into 3,4-bis(lithiomethyl)dihydropyrrole intermediates capable of reacting with carboxylic esters and Weinreb amides. These ketopyrroles have demonstrated to
be excellent precursors of mono or bis(alkynols)pyrroles that, under gold-catalysis, experience a
benzannulation reaction providing access to regioselectively substituted indoles or carbazoles.
2023-02-07T13:34:36Z
2023-02-07T13:34:36Z
2022-09
info:eu-repo/semantics/article
1615-4150
http://hdl.handle.net/10259/7416
10.1002/adsc.202200824
1615-4169
eng
Advanced Synthesis & Catalysis. 2022, V. 364, n. 21, p. 3716-3724
https://doi.org/10.1002/adsc.202200824
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-115789GB-C21/ES/ESTRATEGIAS SINTETICAS SOSTENIBLES PARA LA TRANSFORMACION DIRECTA DE NITROCOMPUESTOS Y DESARROLLO DE NUEVAS REACCIONES CATALIZADAS POR ORO/
info:eu-repo/grantAgreement/Junta de Castilla y León//BU049P20//Estrategias sintéticas sostenibles para la halogenación directa de nitrocompuestos y la preparación de electrolitos orgánicos para baterías de flujo redox/
info:eu-repo/grantAgreement/Fundación Bancaria Caixa d'Estalvis i Pensions de Barcelona//LCF%2FPR%2FPR18%2F51130007// Fluoración Directa de Nitrocompuestos y Sales de Heteroaril Fosfonio: Síntesis de Fluorocompuestos/FluNitroPhos/
http://creativecommons.org/licenses/by-nc/4.0/
info:eu-repo/semantics/openAccess
Atribución-NoComercial 4.0 Internacional
Wiley