Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10259/7416
Título
“Back‐to‐Front” Indole and Carbazole Synthesis from N,N‐Bis‐(2‐bromoallyl)amines by Combining Carbolithiation Reactions with Gold‐Catalysis
Autor
Publicado en
Advanced Synthesis & Catalysis. 2022, V. 364, n. 21, p. 3716-3724
Editorial
Wiley
Fecha de publicación
2022-09
ISSN
1615-4150
DOI
10.1002/adsc.202200824
Abstract
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.
Palabras clave
Carbolithiation
Gold
Homogeneous catalysis
Nitrogen heterocycles
Organolithiums
Materia
Química analítica
Chemistry, Analytic
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