Bimetallic Catalyzed Synthesis of 2-Arylindoles

Author:

Marques M. Manuel B.1ORCID,Ferro Rita1,Viduedo Nuno1,Santos A. Sofia12,Silva Artur M. S.2ORCID,Royo Beatriz3

Affiliation:

1. LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, Universidade Nova de Lisboa

2. LAQV@REQUIMTE, Department of Chemistry, University of Aveiro

3. ITQB NOVA, Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa

Abstract

AbstractA 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.

Funder

Fundação para a Ciência e a Tecnologia

Fundação para a Ciência e a Tecnologia/Ministério da Ciência

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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