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Synthesis 2022; 54(03): 741-753
DOI: 10.1055/s-0041-1737275
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
Projects of national interest (Progetti di Ricerca di Interesse Nazionale - PRIN 2017SXBSX4) project 2017 ‘Targeting Hedgehog pathway: virtual screening identification and sustainable synthesis of novel Smo and Gli inhibitors and their pharmacological drug delivery strategies for improved therapeutic effects in tumors.’
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
palladium - boronic acids - Suzuki–Miyaura reaction - indoles - benzofurans - diarylmethanesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737275.
- Supporting Information
Publication History
Received: 15 August 2021
Accepted after revision: 07 October 2021
Article published online:
11 November 2021
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For biological activity of benzylated indoles, see: