Novel organotin-PTA complexes supported on mesoporous carbon materials as recyclable catalysts for solvent-free cyanosilylation of aldehydes

New organotin compounds with general formula [(PTA-CH2-C6H4-p-COO)SnR3]Br (where R is Me for 3 and Ph for 4; PTA = 1,3,5-triaza-7-phosphaadamantane), bearing the methylene benzoate PTA derivative, were synthesized through a mild two-step process. The compounds were characterized by Fourier transform infrared spectroscopy, electrospray ionization mass spectrometry, elemental analysis and nuclear magnetic resonance spectroscopy (NMR). They were heterogenized on commercially available activated carbon (AC) and multi-walled carbon nanotubes (CNT), as well as on their chemically modified analogues. The obtained materials were characterized by scanning electron microscopy, transmission electron microscopy and X-ray photoelectron spectroscopy. Complex 3 supported on activated carbon (3-AC) was found to be an active and recyclable catalyst for the cyanosilylation of several aromatic and aliphatic aldehydes. Using 3-AC with a low loading of 0.1 mol% several substrates were quantitatively converted, within just 5 min at 50 °C and under microwave irradiation in solvent-free conditions. Multinuclear NMR analysis suggested a mechanism that potentially involves a double activation process, where the nucleophilic phosphorus at the PTA derivative acts as a Lewis base and the Sn(IV) metal centre as a Lewis acid. © 2023 Elsevier B.V.

Authors
Mahmoud A.G. , Librando I.L. , Paul A. , Carabineiro S.A.C. , Ferraria A.M. , Botelho do Rego A.M. , Guedes da Silva M.F.C. , Geraldes C.F.G.C. , Pombeiro A.J.L.
Journal
Catalysis Today
Publisher
Elsevier
Language
English
Status
Published
Link
External link
DOI
10.1016/J.CATTOD.2023.114270
Number
114270
Volume
423
Year
2023
Organizations
  • 1 Centro de Química Estrutural, Institute of Molecular Sciences, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisboa, 1049-001, Portugal
  • 2 Department of Chemistry, Faculty of Science, Helwan University, Ain Helwan, Cairo, 11795, Egypt
  • 3 Department of Chemistry, Mindanao State University-Iligan Institute of Technology, Tibanga, Iligan City, 9200, Philippines
  • 4 LAQV-REQUIMTE, Department of Chemistry, Nova School of Science and Technology, Universidade Nova de Lisboa, Caparica, 2829-516, Portugal
  • 5 LSRE-LCM – Laboratory of Separation and Reaction Engineering – Laboratory of Catalysis and Materials, Faculty of Engineering, University of Porto, Rua Dr. Roberto Frias, Porto, 4200-465, Portugal
  • 6 BSIRG, IBB - Institute for Bioengineering and Biosciences, Instituto Superior Técnico, Universidade de Lisboa, Lisboa, 1049-001, Portugal
  • 7 Associate Laboratory i4HB—Institute for Health and Bioeconomy at Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisboa, 1049-001, Portugal
  • 8 Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisboa, 1049-001, Portugal
  • 9 Department of Life Sciences, Faculty of Science and Technology, Calçada Martim de Freitas, Coimbra, 3000-393, Portugal
  • 10 Coimbra Chemistry Center, University of Coimbra, Rua Larga Largo D. Dinis, Coimbra, 3004-535, Portugal
  • 11 Peoples’ Friendship University of Russia (RUDN University), Research Institute of Chemistry, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
Keywords
1,3,5-triaza-7-phosphaadamantane; Carbon materials; Cyanosilylation; Heterogeneous catalysis; Microwave; Tetrel σ-hole bond
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