Bimetallic Catalyzed Synthesis of 2-Arylindoles

R. Ferro; N. Viduedo; A. S. Santos; A. M. S Silva; B Royo; M. M. B Marques

doi:10.1055/a-2035-6420

Bimetallic Catalyzed Synthesis of 2-Arylindoles

R. Ferro, N. Viduedo, A. S. Santos, A. M. S Silva, B Royo, M. M. B Marques

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

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.

Original language	English
Number of pages	7
Journal	Synthesis-Stuttgart
Early online date	17 Mar 2023
DOIs	https://doi.org/10.1055/a-2035-6420
Publication status	Published - 2 Nov 2023

Keywords

C-H activation
Bimetallic catalysis
Indole
Manganese
Nickel
Oxidation
Palladium

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10.1055/a-2035-6420

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title = "Bimetallic Catalyzed Synthesis of 2-Arylindoles",

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.",

keywords = "C-H activation, Bimetallic catalysis, Indole, Manganese, Nickel, Oxidation, Palladium",

author = "R. Ferro and N. Viduedo and Santos, {A. S.} and Silva, {A. M. S} and B Royo and Marques, {M. M. B}",

note = "The authors thank the Funda{\c c}{\~a}o para a Ci{\^e}ncia 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 Laborat{\'o}rio Associado para a Qu{\'i}mica Verde (LAQV), which is financed by national funds from FCT/Minist{\'e}rio da Ci{\^e}ncia, 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).",

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AU - Viduedo, N.

AU - Santos, A. S.

AU - Silva, A. M. S

AU - Royo, B

AU - Marques, M. M. B

N1 - 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).

PY - 2023/11/2

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N2 - 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.

AB - 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.

KW - C-H activation

KW - Bimetallic catalysis

KW - Indole

KW - Manganese

KW - Nickel

KW - Oxidation

KW - Palladium

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Bimetallic Catalyzed Synthesis of 2-Arylindoles

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Keywords

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