Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst

STEINGRUBER, H. SEBASTIÁN; MENDIOROZ, PAMELA; VOLPE, MARÍA A.; GERBINO, DARÍO C.

SYNTHESIS-STUTTGART

GEORG THIEME VERLAG KG

Año: 2021 vol. 53 p. 4048 - 4058

0039-7881

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.