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

Dedicated to Professor Julio C. Podestá on the occasion of his 80^th birthday

Abstract

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.

Key words

carbazoles - tandem reaction - microwave-assisted synthesis - heterogeneous catalyst - synthetic methods

Publication History

Received: 19 May 2021

Accepted after revision: 21 June 2021

Article published online:
22 July 2021

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