{"title":"Base-promoted hydrophosphination of in situ formed aza-ortho-quinone methides for the preparation of 2-aminobenzyl phosphorus oxides","authors":"Mengjie Gong , Fuxing Yang , Nan Huang, Jun Jiang","doi":"10.1016/j.tetlet.2025.155658","DOIUrl":null,"url":null,"abstract":"<div><div>A base-promoted 1,4-hydrophosphination of <em>in situ</em> generated aza-<em>ortho</em>-quinone methides (aza-<em>o</em>-QMs) from <em>N</em>-(<em>ortho</em>-chloromethyl)aryl amides was reported in this work. Diarylphosphine oxides and phosphites serve as efficient P-nucleophiles in these reactions. The advantages of this method include a broad substrate scope, operational simplicity, mild conditions, and high yields, providing an alternative strategy for synthesizing various 2-aminobenzyl phosphorus oxides.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"165 ","pages":"Article 155658"},"PeriodicalIF":1.5000,"publicationDate":"2025-05-15","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/S0040403925002072","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A base-promoted 1,4-hydrophosphination of in situ generated aza-ortho-quinone methides (aza-o-QMs) from N-(ortho-chloromethyl)aryl amides was reported in this work. Diarylphosphine oxides and phosphites serve as efficient P-nucleophiles in these reactions. The advantages of this method include a broad substrate scope, operational simplicity, mild conditions, and high yields, providing an alternative strategy for synthesizing various 2-aminobenzyl phosphorus oxides.
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.