Download PDF
Synthesis 2021; 53(07): 1301-1306
DOI: 10.1055/s-0040-1705938
paper

Palladium Nanoparticles Anchored on Magnesium Organosilicate: An Effective and Selective Catalyst for the Heck Reaction

Beatriz F. dos Santos
a   Organic Catalysis and Biocatalysis Laboratory – LACOB, Federal University of Grande Dourados – UFGD, Dourados/MS, Brazil   Email: nelsondomingues@ufgd.edu.br
,
Beatriz A. L. da Silva 
a   Organic Catalysis and Biocatalysis Laboratory – LACOB, Federal University of Grande Dourados – UFGD, Dourados/MS, Brazil   Email: nelsondomingues@ufgd.edu.br
,
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
,
Andrelson W. Rinaldi
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   Email: nelsondomingues@ufgd.edu.br
› Author AffiliationsThe author N.L.C.D thanks the 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 the 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, the authors N.L.C.D. and B.F.S thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES/Brazil) for a research fellowship (Auxílio No 2209/2015, Processo No 23038.008241/2014-89, Programa CAPES-FAPCO) and a scholarship.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

A new and effective palladium catalyst supported on a magnesium organosilicate for application in the Heck reaction is presented. A group of compounds comprising 22 examples were synthesized in moderate to high yields (up to 99%) within a short time. The palladium supported on magnesium organosilicate catalyst was characterized as an amorphous solid by SEM, containing around 33% of palladium inside the solid, and even with this low quantity of palladium, the catalyst was very efficient in the Heck reaction. Besides, based on the Scherrer equation, the crystallite size of the synthesized palladium nanoparticles was ultrasmall (around 1.3 nm). This strategy is a simple and efficient route for the formation of C–C bonds via the Heck cross-coupling reaction.

Key words

cross-coupling - Heck reaction - palladium - heterogeneous catalyst - organosilicates

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705938.
  • Supporting Information


Publication History

Received: 25 June 2020

Accepted after revision: 16 September 2020

Article published online:
22 October 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Karimi B, Enders D. Org. Lett. 2006; 8: 1237
    CrossrefPubMed
    • 2a Trost BM, Knopf JD, Brindle CS. Chem. Rev. 2016; 116: 15035
      CrossrefPubMed
    • 2b Rousée K, Bouillon J.-P, Couve-Bonnaire S, Pannecoucke X. Org. Lett. 2016; 18: 540
      CrossrefPubMed
  • 3 Aukland MH, Talbot FJ. T, Fernández-Salas JA, Ball M, Pulis AP, Procter DJ. Angew. Chem. Int. Ed. 2018; 57: 9785 ; Angew. Chem. 2018, 130, 9933
    CrossrefPubMed
  • 4 Patel HH, Sigman MS. J. Am. Chem. Soc. 2015; 137: 3462
    CrossrefPubMed
  • 5 Liu X.-L, Li B, Gu Z.-H. J. Org. Chem. 2015; 80: 7547
    CrossrefPubMed
  • 6 Cong H, Fu GC. J. Am. Chem. Soc. 2014; 136: 3788
    CrossrefPubMed
  • 7 Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
    CrossrefPubMed
  • 8 Sun R, Liu B, Li B.-G, Jie S. ChemCatChem 2016; 8: 3261
    Crossref
  • 9 Wali A, Pillai SM, Satish S. React. Kinet. Catal. Lett. 1997; 60: 189
    Crossref
  • 10 Khajehzadeh M, Moghadam M. J. Organomet. Chem. 2018; 863: 60
    Crossref
  • 11 Liu Y, Bai X, Li S. Microporous Mesoporous Mater. 2018; 260: 40
    Crossref
  • 12 Taher A, Lee D.-J, Lee I.-M, Rahman ML, Sarker MS. Bull. Korean Chem. Soc. 2016; 37: 1478
    Crossref
  • 13 Sato T, Ohno A, Sarkar SM, Uozumi Y, Yamada YM. A. ChemCatChem 2015; 7: 2141
    Crossref
  • 14 Ghorbani-Choghamarani A, Tahmasbi B, Noori N, Faryadi S. C. R. Chim. 2017; 20: 132
    Crossref
  • 15 Huang L, Subramanian R, Wang J, Kwon Oh J, Ye Z. Mol. Catal. 2020; 488: 110923
    Crossref
  • 16 Yu L, Huang Y, Wei Z, Ding Y, Su C, Xu Q. J. Org. Chem. 2015; 80: 8677
    CrossrefPubMed
  • 17 Patel HA, Sharma SK, Jasra RV. J. Mol. Catal. A: Chem. 2008; 286: 31
    Crossref
  • 18 Moura KO, Pastore HO. Microporous Mesoporous Mater. 2014; 190: 292
    Crossref
    • 19a Houdayer A, Schneider R, Billaud D, Ghanbaja J, Lambert J. Appl. Organomet. Chem. 2005; 19: 1239
      Crossref
    • 19b Somjit V, Wong Chi Man M, Ouali A, Sangtrirutnugul P, Ervithayasuporn V. ChemistrySelect 2018; 3: 753
      CrossrefPubMed
    • 20a Jagtap S. Catalysts 2017; 7: 267
    • 20b Sherwood J, Clark JH, Fairlamb IJ. S, Slattery JM. Green Chem. 2019; 21: 2164
      Crossref
  • 21 Khan M, Khan M, Kuniyil M, Adil SF, Al-Warthan A, Alkhathlan HZ, Tremel W, Tahir MN, Siddiqui MR. H. Dalton Trans. 2014; 43: 9026
    CrossrefPubMed
  • 22 Xuan S, Jiang W, Gong X. Dalton Trans. 2011; 40: 7827
    CrossrefPubMed
  • 23 Mekkaoui AA, Jennane S, Aberkouks A, Boualy B, Mehdi A, Ait Ali M, El Firdoussi L, El Houssame S. Appl. Organomet. Chem. 2019; 33: e5117
    Crossref
  • 24 Sore HF, Boehner CM, MacDonald SJ. F, Norton D, Fox DJ, Spring DR. Org. Biomol. Chem. 2009; 7: 1068
    CrossrefPubMed
  • 25 Okita T, Asahara KK, Muto K, Yamaguchi J. Org. Lett. 2020; 22: 3205
    CrossrefPubMed
  • 26 Ghasemzadeh MS, Akhlaghinia B. Aust. J. Chem. 2019; 72: 674
    Crossref
  • 27 Ren G, Cui X, Yang E, Yang F, Wu Y. Tetrahedron 2010; 66: 4022
    Crossref
  • 28 Shao-Hsien H. Molecules 2010; 15: 315
    CrossrefPubMed
  • 29 Wei Y.-L, Li Y, Chen Y.-Q, Dong Y, Yao J.-J, Han X.-Y, Dong Y.-B. Inorg. Chem. 2018; 57: 4379
    CrossrefPubMed
  • 30 Balinge KR, Bhagat PR. Inorg. Chim. Acta 2019; 495: 119017
    Crossref