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基于碲化镉的柱[5]芳烃：一种用于水溶液中烷基化反应的可循环催化剂。

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

作者信息

Nobre Patrick C, Cordeiro Pâmella, Chipoline Ingrid C, Menezes Victor, Santos Kaila V S, Ángel Alix Y Bastidas, Alberto Eduardo E, Nascimento Vanessa

机构信息

SupraSelen Laboratory, Department of Organic Chemistry, Universidade Federal Fluminense, Campus do Valonguinho, Niterói, Rio de Janeiro 24020-141, Brazil.

Departamento de Química, Universidade Federal de Minas Gerais-UFMG, Belo Horizonte, Minas Gerais 31270-901, Brazil.

出版信息

J Org Chem. 2024 Sep 20;89(18):12982-12988. doi: 10.1021/acs.joc.4c00997. Epub 2024 Sep 4.

DOI:10.1021/acs.joc.4c00997
PMID:39233358
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11421007/
Abstract

The syntheses of previously unknown sulfide- and telluride-pillar[]arenes are reported here. These macrocycles, among others, were tested as catalysts for alkylation reactions in aqueous solutions. Telluride-pillar[5]arene () showed the best performance, emulating the behavior of the methyltransferase enzyme cofactor -adenosyl-l-methionine. Using 1.0 mol % of , benzyl bromides reacted with NaCN/NaN in water, yielding organic nitriles/azides. The catalyst was recycled and efficiently reused for up to six cycles. H NMR experiments indicate a possible interaction between the substrate and 's cavity.

摘要

本文报道了此前未知的硫化物和碲化物柱芳烃的合成。这些大环化合物等被测试作为水溶液中烷基化反应的催化剂。碲化物柱[5]芳烃（）表现出最佳性能，模拟了甲基转移酶辅因子 -腺苷-L-甲硫氨酸的行为。使用1.0 mol%的，苄基溴在水中与NaCN/NaN反应，生成有机腈/叠氮化物。该催化剂可循环使用，高效重复使用多达六个循环。核磁共振氢谱实验表明底物与的空腔之间可能存在相互作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/cb26d2ec2676/jo4c00997_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/ba177cae8447/jo4c00997_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/65baac229583/jo4c00997_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/d730604ab8fc/jo4c00997_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/212f37d81b4f/jo4c00997_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/cb26d2ec2676/jo4c00997_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/ba177cae8447/jo4c00997_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/65baac229583/jo4c00997_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/d730604ab8fc/jo4c00997_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/212f37d81b4f/jo4c00997_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/308f/11421007/cb26d2ec2676/jo4c00997_0005.jpg

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本文引用的文献

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2
Selenonium Salt as a Catalyst for Nucleophilic Substitution Reactions in Water: Synthesis of Thiocyanites and Selenocyanates.硒𬭩盐作为水相亲核取代反应的催化剂：硫氰酸盐和硒氰酸盐的合成。
Molecules. 2023 Mar 29;28(7):3056. doi: 10.3390/molecules28073056.
3
Pillararenes as Promising Carriers for Drug Delivery.
多环芳烃作为有前途的药物传递载体。
Int J Mol Sci. 2023 Mar 8;24(6):5167. doi: 10.3390/ijms24065167.
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Synthetic application of chalcogenonium salts: beyond sulfonium.硫属鎓盐的合成应用：超越锍盐。
Org Biomol Chem. 2023 Jan 4;21(2):223-236. doi: 10.1039/d2ob01822e.
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Solid Lipid Nanoparticles Based on Monosubstituted Pillar[5]arenes: Chemoselective Synthesis of Macrocycles and Their Supramolecular Self-Assembly.基于单取代柱[5]芳烃的固体脂质纳米颗粒：大环化合物的化学选择性合成及其超分子自组装
Nanomaterials (Basel). 2022 Nov 30;12(23):4266. doi: 10.3390/nano12234266.
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