Telluride-Based Pillar[5]arene: A Recyclable Catalyst for Alkylation Reactions in Aqueous Solution.

Autor: Nobre PC; SupraSelen Laboratory, Department of Organic Chemistry, Universidade Federal Fluminense, Campus do Valonguinho, Niterói, Rio de Janeiro 24020-141, Brazil., Cordeiro P; SupraSelen Laboratory, Department of Organic Chemistry, Universidade Federal Fluminense, Campus do Valonguinho, Niterói, Rio de Janeiro 24020-141, Brazil., Chipoline IC; SupraSelen Laboratory, Department of Organic Chemistry, Universidade Federal Fluminense, Campus do Valonguinho, Niterói, Rio de Janeiro 24020-141, Brazil., Menezes V; SupraSelen Laboratory, Department of Organic Chemistry, Universidade Federal Fluminense, Campus do Valonguinho, Niterói, Rio de Janeiro 24020-141, Brazil., Santos KVS; SupraSelen Laboratory, Department of Organic Chemistry, Universidade Federal Fluminense, Campus do Valonguinho, Niterói, Rio de Janeiro 24020-141, Brazil., Ángel AYB; Departamento de Química, Universidade Federal de Minas Gerais-UFMG, Belo Horizonte, Minas Gerais 31270-901, Brazil., Alberto EE; Departamento de Química, Universidade Federal de Minas Gerais-UFMG, Belo Horizonte, Minas Gerais 31270-901, Brazil., Nascimento V; SupraSelen Laboratory, Department of Organic Chemistry, Universidade Federal Fluminense, Campus do Valonguinho, Niterói, Rio de Janeiro 24020-141, Brazil.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Sep 20; Vol. 89 (18), pp. 12982-12988. Date of Electronic Publication: 2024 Sep 04.
DOI: 10.1021/acs.joc.4c00997
Abstrakt: The syntheses of previously unknown sulfide- and telluride-pillar[ n ]arenes are reported here. These macrocycles, among others, were tested as catalysts for alkylation reactions in aqueous solutions. Telluride-pillar[5]arene ( P[5]-TePh ) showed the best performance, emulating the behavior of the methyltransferase enzyme cofactor S -adenosyl-l-methionine. Using 1.0 mol % of P[5]-TePh , benzyl bromides reacted with NaCN/NaN 3 in water, yielding organic nitriles/azides. The catalyst was recycled and efficiently reused for up to six cycles. 1 H NMR experiments indicate a possible interaction between the substrate and P[5]-TePh 's cavity.
Databáze: MEDLINE
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