Telluride-Based Pillar[5]arene: A Recyclable Catalyst for Alkylation Reactions in Aqueous Solution
The syntheses of previously unknown sulfide- and telluride-pillar[<i>n</i>]arenes are reported here. These macrocycles, among others, were tested as catalysts for alkylation reactions in aqueous solutions. Telluride-pillar[5]arene (<b>P[5]-TePh</b>) showed the best performance, emulating the behavior of the methyltransferase enzyme cofactor <i>S</i>-adenosyl-l-methionine. Using 1.0 mol % of <b>P[5]-TePh</b>, benzyl bromides reacted with NaCN/NaN<sub>3</sub> in water, yielding organic nitriles/azides. The catalyst was recycled and efficiently reused for up to six cycles. <sup>1</sup>H NMR experiments indicate a possible interaction between the substrate and <b>P[5]-TePh</b>'s cavity.
Authors
- Pâmella Cordeiro (ORCID: https://orcid.org/0000-0002-3644-1786)
- Alix Y. Bastidas Ángel (ORCID: https://orcid.org/0000-0002-8588-5869)
- Patrick C. Nobre (ORCID: https://orcid.org/0000-0003-2050-2684)
- Ingrid C. Chipoline (ORCID: https://orcid.org/0000-0001-7705-2480)
- Eduardo E. Alberto (ORCID: https://orcid.org/0000-0002-5193-1302)
- Vanessa Nascimento (ORCID: https://orcid.org/0000-0001-9413-7638)
- Victor Menezes (ORCID: https://orcid.org/0000-0002-6636-5593)
- Kaila V. S. Santos
Institutions
- Universidade Federal de Minas Gerais (BR)
- Universidade Federal Fluminense (BR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-09-05
- DOI
- https://doi.org/10.1021/acs.joc.4c00997
- Citations
- 4
- Primary Topic
- Crystallography and molecular interactions
- Type
- article
- Field-Weighted Citation Impact
- 1.78
Funders
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro
- Fundação de Amparo à Pesquisa do Estado de Minas Gerais