{"title":"Fe(III)-Catalyzed Intramolecular Hydroamination of 1,3-Dienes Improved by Using Triphenylphosphate as an Additive","authors":"Ye Jin Kim, Dong Bin Kim, So Won Youn","doi":"10.1002/adsc.202401180","DOIUrl":null,"url":null,"abstract":"We herein report that the combination of Fe(OTf)3 and triphenylphosphate (TPP, (PhO)3PO) has proven to be an effective catalyst for the intramolecular hydroamination of amino-1,3-dienes with an efficiency and scope superior to previously reported methods. This catalytic system demonstrated consistent performance with diverse aminodienes as well as aminoolefins, providing five- to seven-membered N-heterocycles. We propose a Lewis/Brønsted acid cocatalysis mechanism involving proton transfer through hydrogen bonding with TPP. Catalyst system consisting of inexpensive and nontoxic iron salt and phosphate additive, relatively low loading and recyclability of catalyst, and rapid and high-yielding reaction are the advantages of this protocol.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":4.4000,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401180","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
We herein report that the combination of Fe(OTf)3 and triphenylphosphate (TPP, (PhO)3PO) has proven to be an effective catalyst for the intramolecular hydroamination of amino-1,3-dienes with an efficiency and scope superior to previously reported methods. This catalytic system demonstrated consistent performance with diverse aminodienes as well as aminoolefins, providing five- to seven-membered N-heterocycles. We propose a Lewis/Brønsted acid cocatalysis mechanism involving proton transfer through hydrogen bonding with TPP. Catalyst system consisting of inexpensive and nontoxic iron salt and phosphate additive, relatively low loading and recyclability of catalyst, and rapid and high-yielding reaction are the advantages of this protocol.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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