{"title":"Copper-catalyzed 1,4-aminohydroxylation and aminothiolation of 1,3-dienes by carbonyl-assisted migration","authors":"Noah H. Watkins, Yungeun Kwon, Qiu Wang","doi":"10.1016/j.checat.2024.101147","DOIUrl":null,"url":null,"abstract":"We report a copper-catalyzed 1,4-selective aminooxygenation of 1,3-dienes as a direct entry to 1,4-allylic amino alcohols. The reactions are effective on a diverse range of amide-, urea-, and ester-containing 1,3-dienes, allowing for the facile installation of aliphatic alkylamines and free alcohol. The transformation was initiated by a copper-catalyzed electrophilic amination using <em>O</em>-benzoylhydroxylamines, and a carbonyl-assisted oxygen migration delivered the exclusive 1,4-selectivity in the subsequent oxygenation step. Inspired by these mechanistic insights, we also realized an unprecedented 1,4-aminothiolation of thioamide-containing 1,3-dienes by leveraging a novel thiol migration.","PeriodicalId":53121,"journal":{"name":"Chem Catalysis","volume":"111 1","pages":""},"PeriodicalIF":11.5000,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chem Catalysis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1016/j.checat.2024.101147","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
We report a copper-catalyzed 1,4-selective aminooxygenation of 1,3-dienes as a direct entry to 1,4-allylic amino alcohols. The reactions are effective on a diverse range of amide-, urea-, and ester-containing 1,3-dienes, allowing for the facile installation of aliphatic alkylamines and free alcohol. The transformation was initiated by a copper-catalyzed electrophilic amination using O-benzoylhydroxylamines, and a carbonyl-assisted oxygen migration delivered the exclusive 1,4-selectivity in the subsequent oxygenation step. Inspired by these mechanistic insights, we also realized an unprecedented 1,4-aminothiolation of thioamide-containing 1,3-dienes by leveraging a novel thiol migration.
期刊介绍：
Chem Catalysis is a monthly journal that publishes innovative research on fundamental and applied catalysis, providing a platform for researchers across chemistry, chemical engineering, and related fields. It serves as a premier resource for scientists and engineers in academia and industry, covering heterogeneous, homogeneous, and biocatalysis. Emphasizing transformative methods and technologies, the journal aims to advance understanding, introduce novel catalysts, and connect fundamental insights to real-world applications for societal benefit.
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