Li Liu, Jun Li, Ya Chen, Shanping Chen, Fuhong Xiao, Guo-Jun Deng
{"title":"Acid-Promoted Amination of Cyclohexenone for the Divergent Synthesis of p-Aminophenols and Tertiary Amines","authors":"Li Liu, Jun Li, Ya Chen, Shanping Chen, Fuhong Xiao, Guo-Jun Deng","doi":"10.1021/acs.joc.4c00292","DOIUrl":null,"url":null,"abstract":"A tunable method for the selective preparation of <i>p</i>-aminophenol and tertiary amines from a secondary amine and cyclohexenone has been described. Nonaromatic cyclohexenones were used as an aryl source. The desired tertiary amine products were generated when using I<sub>2</sub> as the catalyst. This approach yields single-site-selective <i>p</i>-aminophenol without using I<sub>2</sub>, and the <sup>18</sup>O labeling experiments demonstrated that hydroxyl oxygen originates from O<sub>2</sub>.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-18","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.4c00292","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A tunable method for the selective preparation of p-aminophenol and tertiary amines from a secondary amine and cyclohexenone has been described. Nonaromatic cyclohexenones were used as an aryl source. The desired tertiary amine products were generated when using I2 as the catalyst. This approach yields single-site-selective p-aminophenol without using I2, and the 18O labeling experiments demonstrated that hydroxyl oxygen originates from O2.
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.