Palladium-Catalyzed Dehydrogenative Coupling: An Efficient Synthetic Strategy for the Construction of the Quinoline Core

Palladium-catalyzed dehydrogenative coupling is an efficient synthetic strategy for the construction of quinoline scaffolds, a privileged structure and prevalent motif in many natural and biologically active products, in particular in marine alkaloids. Thus, quinolines and 1,2-dihydroquinolines can...

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Bibliographic Details
Authors: Carral Menoyo, Asier, Ortiz de Elguea Flecha, Verónica, Martínez Nunes, Mikel, Sotomayor Anduiza, María Nuria, Lete Expósito, María Esther
Format: article
Publication Date:2017
Country:España
Institution:Universidad del País Vasco
Repository:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/26168
Online Access:http://hdl.handle.net/10810/26168
Access Level:Open access
Keyword:quinoline
synthesis
palladium
coupling
C-H alkenylation
marine natural-products
C-H functionalization
pyridoacridine alkalloids
bond functionalization
indole-derivatives
alkenylation
heterocycles
olefination
cyclization
selectivity
Description
Summary:Palladium-catalyzed dehydrogenative coupling is an efficient synthetic strategy for the construction of quinoline scaffolds, a privileged structure and prevalent motif in many natural and biologically active products, in particular in marine alkaloids. Thus, quinolines and 1,2-dihydroquinolines can be selectively obtained in moderate-to-good yields via intramolecular C-H alkenylation reactions, by choosing the reaction conditions. This methodology provides a direct method for the construction of this type of quinoline through an efficient and atom economical procedure, and constitutes significant advance over the existing procedures that require preactivated reaction partners.