Copper-Catalyzed Three-Component Formal [3 + 1 + 2] Benzannulation for Carbazole and Indole Synthesis

Autor:	Tingpeng Wang, Lan Lei, Jian Zhang, Tenglong Guo, Li Han, Dezhu Xu
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Ketone chemistry 010405 organic chemistry Component (thermodynamics) Organic Chemistry Copper catalyzed Molecule Aggregation-induced emission 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences
Zdroj:	The Journal of Organic Chemistry. 85:9117-9128
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.0c01056
Popis:	Three-component formal [3 + 1 + 2] benzannulation reactions of indole-3-carbaldehydes or 1-methyl-pyrrole-2-carbaldehydes with two different molecules of saturated ketones have been successfully developed under Cu-catalyzed and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated conditions. Various unsymmetrically substituted carbazoles and indoles were obtained up to 95% yield. Furthermore, the resulting products exhibit unusual aggregation-induced emission (AIE) properties in the solid state. This method features high atom-economy, cheap catalysts and oxidants, wide substrate scope, and saturated ketones as one-carbon and two-carbon sources, thus providing an efficient approach to polycyclic carbazole and indole compounds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1068ecf725dc0c93a03d090057b6a383 https://doi.org/10.1021/acs.joc.0c01056 Zobrazit plný text záznamu