Synthesis, Table of Contents

Synthesis 2022; 54(03): 741-753
DOI: 10.1055/s-0041-1737275

paper

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

Antonio Arcadi

^aDipartimento di Ingegneria e Scienze dell’Informazione e Matematica, Università degli studi di L’ Aquila, Via Vetoio, 67100 Coppito (AQ), Italy

^bDipartimento di Scienze Fisiche e Chimiche, Università degli studi di L’ Aquila, Via Vetoio, 67100 Coppito (AQ), Italy

,

Andrea Calcaterra

^cDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy

,

Marco Chiarini

^dUniversità degli Studi di Teramo, Facoltà di Bioscienze e tecnologie agro-alimentari e ambientali, via R. Balzarini, 1 - 64100 Teramo, Italy

,

Giancarlo Fabrizi

^cDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy

,

Andrea Fochetti

^cDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy

,

Antonella Goggiamani∗

^cDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy

,

Antonia Iazzetti ∗

^eDipartimento di Scienze Biotecnologiche di base, Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, L.go Francesco Vito 1, 00168 Rome, Italy

,

Federico Marrone

^cDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy

,

Vincenzo Marsicano

^bDipartimento di Scienze Fisiche e Chimiche, Università degli studi di L’ Aquila, Via Vetoio, 67100 Coppito (AQ), Italy

,

Andrea Serraiocco

^cDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy

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Abstract

The palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η³-C₃H₅)Cl]₂/XPhos while with benzofuranylmethyl acetates Pd₂(dba)₃/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

Key words

Key words

palladium - boronic acids - Suzuki–Miyaura reaction - indoles - benzofurans - diarylmethanes

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Supplementary Material

Supplementary Material

Supporting Information