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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

“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 Química analítica Chemistry, Analytic 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. 2023-02-07T13:34:36Z 2023-02-07T13:34:36Z 2022-09 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion 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/ Atribución-NoComercial 4.0 Internacional http://creativecommons.org/licenses/by-nc/4.0/ info:eu-repo/semantics/openAccess application/pdf Wiley