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DOI: 10.1055/a-2035-6420
Bimetallic Catalyzed Synthesis of 2-Arylindoles
Authors
The authors thank the Fundação para a Ciência e Tecnologia (FCT, projects PTDC/QUI-QOR/0712/2020 and PTDC/QUI-QIN/0359/2021, fellowship PD/BD/142876/2018 (A.S.S.)). The authors also thank the support by the Laboratório Associado para a Química Verde (LAQV), which is financed by national funds from FCT/Ministério da Ciência, Tecnologia e Ensino Superior and MOSTMICRO-ITQB, UIDB/04612/2020 and UIPD/04612/2020. The National NMR Facility is supported by FCT, ROTEIRO/0031/2013–PINFRA/22161/2016, co-financed by FEDER through COMPETE 2020, POCI, and PORL and FCT through PID-DAC) and CERMAX (022162).
Abstract
A bimetallic synthesis of 2-arylindoles from alcohols and anilines is described. The dehydrogenation or oxidation of a secondary alcohol was performed by Ni- or Mn-catalyzed reactions, respectively. The formed ketone was converted into an imine intermediate that was later cyclized to the corresponding 2-arylindole by a Pd-catalyzed oxidative cyclization. A series of 2-arylindoles were prepared without isolation of the intermediates generated. The compatibility of the catalysts was investigated, and the optimized protocol opens room for the integration of Earth-abundant metals and palladium complexes to improve the sustainability of the synthesis of N-heterocycles.
Key words
manganese - nickel - palladium - bimetallic catalysis - indole - oxidation - C–H activationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2035-6420.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 03. November 2022
Angenommen nach Revision: 14. Februar 2023
Accepted Manuscript online:
14. Februar 2023
Artikel online veröffentlicht:
17. März 2023
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