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

H. Sebastián Steingruber; Pamela Mendioroz; María A. Volpe; Darío C. Gerbino

doi:10.1055/s-0037-1610778

Synthesis, Table of Contents

Synthesis 2021; 53(21): 4048-4058
DOI: 10.1055/s-0037-1610778

paper

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

H. Sebastián Steingruber

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina

,

Pamela Mendioroz

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina

,

María A. Volpe

^bPlanta Piloto de Ingeniería Química (PLAPIQUI-CONICET), Camino La Carrindanga Km 7, 8000 Bahía Blanca, Argentina

,

Darío C. Gerbino∗

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina

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Abstract

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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

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