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Title: | Novel organotin-PTA complexes supported on mesoporous carbon materials as recyclable catalysts for solvent-free cyanosilylation of aldehydes | Authors: | Mahmoud, Abdallah G. Librando, Ivy L. Paul, Anup Carabineiro, Sónia A. C. Ferraria, Ana Maria Botelho do Rego, Ana Maria Guedes da Silva, M. Fátima C. Geraldes, Carlos F. G. C. Pombeiro, Armando J. L. |
Keywords: | Cyanosilylation; Carbon materials; Heterogeneous catalysis; 1,3,5-triaza-7-phosphaadamantane; Microwave; Tetrel σ-hole bond | Issue Date: | 2023 | Publisher: | Elsevier | Project: | The authors are grateful for the financial support from Fundaç˜ao para a Ciˆencia e a Tecnologia (FCT), Portugal, through projects UIDB/ 00100/2020, UIDP/00100/2020 and LA/P/0056/2020 of Centro de Quίmica Estrutural; projects UIDB/04565/2020, UIDP/04565/2020, and LA/P/0140/2020 of Institute for Bioengineering and Biosciences – iBB and the Associate Laboratory Institute for Health and Bioeconomy - i4HB and projects UIDB/50020/2020 and UIDP/50020/2020 (LSRELCM). The work was also funded by national funds through FCT, under the Scientific Employment Stimulus-Institutional Call (CEEC-INST/ 00102/2018). We also acknowledge the Associate Laboratory for Green Chemistry – LAQV financed by national funds from FCT/MCTES (UIDB/ 50006/2020 and UIDP/5006/2020) and Base-UIDB/50020/ 2020 and Programmatic UIDP/50020/2020 funding of the Associate Laboratory LSRE-LCM. AGM is grateful to Associaç˜ao do Instituto Superior T´ecnico para a Investigaç˜ao e Desenvolvimento (IST-ID) for his post-doctoral fellowship through grant no. BL133/2021-IST-ID. ILL acknowledges the CATSUS PhD Program from FCT for her grant PD/BD/135555/2018. AP and AMF are grateful to FCT and Instituto Superior T´ecnico (IST), Portugal through DL/57/2017 (Contract no. IST-ID/197/2019 and ISTID/ 131/2018). This publication is also supported by the RUDN University Strategic Academic Leadership Program (recipient AJLP, preparation). The authors also acknowledge the Portuguese NMR Network (IST-UL Centre) for access to the NMR facility. CFGCG thanks the FCT for funding of CQC-IMS through the projects UIDB/ 00313/2020 and UIDP/ 00313/2020. | Serial title, monograph or event: | Catalysis Today | Volume: | 423 | Abstract: | 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 multiwalled 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. | URI: | https://hdl.handle.net/10316/111857 | ISSN: | 09205861 | DOI: | 10.1016/j.cattod.2023.114270 | Rights: | openAccess |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais FCTUC Ciências da Vida - Artigos em Revistas Internacionais |
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