2026-06-19T13:03:53Zhttps://riubu.ubu.es/oai/request

oai: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

Muñoz Torres, Miguel Ángel Martínez Lara, Fernando Solas Luera, Marta Suarez Pantiga, Samuel Sanz Díez, Roberto 2023-02-07T13:34:36Z 2023-02-07T13:34:36Z 2022-09 1615-4150 http://hdl.handle.net/10259/7416 10.1002/adsc.202200824 1615-4169 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. We gratefully acknowledge Ministerio de Ciencia e Innovación MCIN/AEI/10.13039/501100011033 (PID2020-115789GBC21), and Junta de Castilla y León and FEDER (BU049P20) for financial support. The project leading to these results has received funding from “la Caixa” Foundation, under the Agreement LCF/PR/PR18/51130007> (CAIXA-UBU001). M.A.M., F.M.-L., M.S. and S.S.-P. thank Junta de Castilla y León (Consejería de Educación) and Fondo Social Europeo for predoctoral (M.A.M, F.M.-L. and M.S.) and postdoctoral (S.S.- P.) contracts, respectively. application/pdf eng Wiley 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/ Atribución-NoComercial 4.0 Internacional http://creativecommons.org/licenses/by-nc/4.0/ info:eu-repo/semantics/openAccess Carbolithiation Gold Homogeneous catalysis Nitrogen heterocycles Organolithiums Química analítica Chemistry, Analytic “Back‐to‐Front” Indole and Carbazole Synthesis from N,N‐Bis‐(2‐bromoallyl)amines by Combining Carbolithiation Reactions with Gold‐Catalysis info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Advanced Synthesis & Catalysis 364 21 3716 3724