Jéssica O. Figueiredo , Emily M. Porto , Marcelo H.R. Carvalho , Daniel M. Araújo , Guilherme M. Martins , Giovanni W. Amarante , Pedro P. de Castro
{"title":"有机催化和有机电合成作为姜酮制备的替代方法","authors":"Jéssica O. Figueiredo , Emily M. Porto , Marcelo H.R. Carvalho , Daniel M. Araújo , Guilherme M. Martins , Giovanni W. Amarante , Pedro P. de Castro","doi":"10.1016/j.tetlet.2025.155772","DOIUrl":null,"url":null,"abstract":"<div><div>This study presents a novel and efficient method for synthesizing zingerone through a combination of organocatalysis and organic electrosynthesis. The process begins with the aldol condensation of vanillin and acetone using <em>in situ</em> generated morpholinium trifluoroacetate organocatalyst. This step is followed by the electrochemical reduction of the resulting enone intermediate using a simple setup employing graphite electrodes, KBr as electrolyte and water as the proton source. This approach allows for a simple and safe strategy to access zingerone, significantly enhancing the reaction's efficiency. Notably, the method's simplicity eliminates the need for hazardous reagents and solvents, making it an environmentally friendly alternative.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155772"},"PeriodicalIF":1.5000,"publicationDate":"2025-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Organocatalysis and organic electrosynthesis as an alternative for zingerone preparation\",\"authors\":\"Jéssica O. Figueiredo , Emily M. Porto , Marcelo H.R. Carvalho , Daniel M. Araújo , Guilherme M. Martins , Giovanni W. Amarante , Pedro P. de Castro\",\"doi\":\"10.1016/j.tetlet.2025.155772\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>This study presents a novel and efficient method for synthesizing zingerone through a combination of organocatalysis and organic electrosynthesis. The process begins with the aldol condensation of vanillin and acetone using <em>in situ</em> generated morpholinium trifluoroacetate organocatalyst. This step is followed by the electrochemical reduction of the resulting enone intermediate using a simple setup employing graphite electrodes, KBr as electrolyte and water as the proton source. This approach allows for a simple and safe strategy to access zingerone, significantly enhancing the reaction's efficiency. Notably, the method's simplicity eliminates the need for hazardous reagents and solvents, making it an environmentally friendly alternative.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"170 \",\"pages\":\"Article 155772\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2025-08-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403925003211\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925003211","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Organocatalysis and organic electrosynthesis as an alternative for zingerone preparation
This study presents a novel and efficient method for synthesizing zingerone through a combination of organocatalysis and organic electrosynthesis. The process begins with the aldol condensation of vanillin and acetone using in situ generated morpholinium trifluoroacetate organocatalyst. This step is followed by the electrochemical reduction of the resulting enone intermediate using a simple setup employing graphite electrodes, KBr as electrolyte and water as the proton source. This approach allows for a simple and safe strategy to access zingerone, significantly enhancing the reaction's efficiency. Notably, the method's simplicity eliminates the need for hazardous reagents and solvents, making it an environmentally friendly alternative.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.