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Synthesis 2021; 53(05): 933-942
DOI: 10.1055/s-0040-1705989
paper

Anchored Pd(0) Nanoparticles on Synthetic Talc for the Synthesis of Biaryls and a Precursor of Angiotensin II Inhibitors

Beatriz F. dos Santos
a   Organic Catalysis and Biocatalysis Laboratory – LACOB, Federal University of Grande Dourados – UFGD, Dourados, MS, Brazil
,
Beatriz A. L. da Silva 
a   Organic Catalysis and Biocatalysis Laboratory – LACOB, Federal University of Grande Dourados – UFGD, Dourados, MS, Brazil
,
Aline R. de Oliveira
b   State University of Maringá – UEM, Maringá, PR, Brazil
,
Maria H. Sarragiotto
b   State University of Maringá – UEM, Maringá, PR, Brazil
,
Nelson Luís C. Domingues  ∗
a   Organic Catalysis and Biocatalysis Laboratory – LACOB, Federal University of Grande Dourados – UFGD, Dourados, MS, Brazil
› Author AffiliationsN.L.C.D. thanks Fundação de Apoio ao Desenvolvimento do Ensino, Ciência e Tecnologia do Estado de Mato Grosso do Sul (FUNDECT/Brazil - Chamada FUNDECT/CNPq Nº 15/2014 - PRONEM - MS) and Conselho Nacional de Desenvolvimento Científico e Tecnológico (Chamada CNPq Nº 12/2017 - Bolsas de Produtividade em Pesquisa - PQ) for financial support and a fellowship. Furthermore, B.F.S. thanks Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES/Brazil) for her scholarship.
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Abstract

The palladium-catalyzed Suzuki–Miyaura cross-coupling reaction is one of the most important and efficient reactions to prepare a variety of organic compounds, including biaryls. Despite the overwhelming number of reports related to this topic, some methodological difficulties persist in terms of catalyst handling, recovery, and reuse, as well as the reaction media. This work reports the rational design of new, efficient, cost-effective, and reusable palladium catalysts supported on synthetic talc for the Suzuki–Miyaura reaction. From the results, key points were identified: both designed catalysts accelerated the reaction in EtOH and an open-flask setup, affording moderate to excellent yields within a short time (e.g., 30 min) even for deactivated aryl halides; the protocol can be applied to a great number of both cross-coupling partners, showing an excellent functional group tolerance; the catalysts can be recovered and reused without significant loss of activity. This protocol was used for the synthesis of a precursor of angiotensin II inhibitors such as valsartan, losartan, irbesartan, and telmisartan.

Key words

cross-coupling - palladium - supported catalysts - Suzuki–Miyaura reaction - synthetic talc

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705989.
  • Supporting Information


Publication History

Received: 22 September 2020

Accepted after revision: 05 November 2020

Article published online:
15 December 2020

© 2020. Thieme. All rights reserved

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