Science and Technology Production
Article
Authorship
Steingruber, Hugo Sebastian
;
MENDIOROZ, PAMELA
;
Volpe, María Alicia
;
GERBINO, DARIO CESAR
Date
2021
Publishing House and Editing Place
GEORG THIEME VERLAG KG
Magazine
SYNTHESIS-STUTTGART,
vol. 53
(pp. 4048-4058)
GEORG THIEME VERLAG KG
Summary
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An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -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 protoco...
An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -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 9 H -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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Key Words
MICROWAVE-ASSISTED SYNTHESISHETEROGENEOUS CATALYSTCARBAZOLESTANDEM REACTIONSYNTHETIC METHODS
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