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Development of a palladium-catalyzed decarboxylative arene cross-coupling of pyrrole derivatives in a flow reactor

Development of a palladium-catalyzed decarboxylative arene cross-coupling of pyrrole derivatives... Palladium-catalyzed decarboxylative cross-coupling was employed to synthesize 2-arylpyrroles via a flow process. This reaction features palladium as the only metal catalyst and uses easily accessible starting materials. The reaction temperature, the residence time, and the quantity of different reactants were investigated to achieve optimal reaction conditions. A variety of N-alkylated and N-arylated 2-arylpyrroles were produced in good to excellent yields. A N-methyl-2-arylpyrrole derivative was produced in 220 min on a 3 g scale in 84% yield. The flow set-up presented in this work is featuring a fixed bed reactor to load the insoluble Cs2CO3 necessary for the decarboxylative cross-coupling to occur, it also comprises a sample loop, and a stainless-steel reactor. This study demonstrated the excellent potential of utilizing a flow process for the synthesis of 2-arylpyrroles derivatives.Graphical abstract[graphic not available: see fulltext] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Development of a palladium-catalyzed decarboxylative arene cross-coupling of pyrrole derivatives in a flow reactor

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Publisher
Springer Journals
Copyright
Copyright © Akadémiai Kiadó 2022
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-022-00222-4
Publisher site
See Article on Publisher Site

Abstract

Palladium-catalyzed decarboxylative cross-coupling was employed to synthesize 2-arylpyrroles via a flow process. This reaction features palladium as the only metal catalyst and uses easily accessible starting materials. The reaction temperature, the residence time, and the quantity of different reactants were investigated to achieve optimal reaction conditions. A variety of N-alkylated and N-arylated 2-arylpyrroles were produced in good to excellent yields. A N-methyl-2-arylpyrrole derivative was produced in 220 min on a 3 g scale in 84% yield. The flow set-up presented in this work is featuring a fixed bed reactor to load the insoluble Cs2CO3 necessary for the decarboxylative cross-coupling to occur, it also comprises a sample loop, and a stainless-steel reactor. This study demonstrated the excellent potential of utilizing a flow process for the synthesis of 2-arylpyrroles derivatives.Graphical abstract[graphic not available: see fulltext]

Journal

Journal of Flow ChemistrySpringer Journals

Published: Jun 7, 2022

Keywords: Decarboxylative cross-coupling; Pyrroles; Palladium-catalyzed reaction; Flow synthesis; Fixed-bed reactor

References