Patrick C Nobre, Pâmella Cordeiro, Ingrid C Chipoline, Victor Menezes, Kaila V S Santos, Alix Y Bastidas Ángel, Eduardo E Alberto, Vanessa Nascimento
{"title":"Telluride-Based Pillar[5]arene: A Recyclable Catalyst for Alkylation Reactions in Aqueous Solution.","authors":"Patrick C Nobre, Pâmella Cordeiro, Ingrid C Chipoline, Victor Menezes, Kaila V S Santos, Alix Y Bastidas Ángel, Eduardo E Alberto, Vanessa Nascimento","doi":"10.1021/acs.joc.4c00997","DOIUrl":null,"url":null,"abstract":"<p><p>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.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c00997","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/4 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
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/NaN3 in water, yielding organic nitriles/azides. The catalyst was recycled and efficiently reused for up to six cycles. 1H NMR experiments indicate a possible interaction between the substrate and P[5]-TePh's cavity.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.