期刊
SYNTHESIS-STUTTGART
卷 53, 期 21, 页码 4048-4058出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610778
关键词
carbazoles; tandem reaction; microwave-assisted synthesis; heterogeneous catalyst; synthetic methods
资金
- National Council of Scientific and Technical Research (Consejo Nacional de Investigaciones Cientificas y Tecnicas
- CONICET)
- National Agency for Scientific and Technological Promotion (Agencia Nacional de Promocion Cientifica y Tecnologica
- ANPCyT)
- Universidad Nacional del Sur (Secretaria General de Ciencia y Tecnologia, Universidad Nacional del Sur
- SGCyT-UNS), Argentina
An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9H-carbazoles under microwave irradiation has been developed, utilizing a novel and magnetically recoverable palladium nanocatalyst supported on green biochar; the methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups.
An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9H-carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9H-carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.
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