T. Mineno, Yukizi Suzuki, Tomoya Nobuta, Daiki Takano, Hisao Kansui
{"title":"在酮介导的氧化酯化过程中用于保护酚功能的基团的相容性","authors":"T. Mineno, Yukizi Suzuki, Tomoya Nobuta, Daiki Takano, Hisao Kansui","doi":"10.4236/gsc.2022.124007","DOIUrl":null,"url":null,"abstract":"Protecting groups often play an essential role in organic synthesis, particularly for multi-step synthesis or natural product total synthesis. Various protecting groups areavailable to mask the vulnerable functionality; phenolic hydroxy groups are noteworthy examples, but their stability differs when protected. Herein, the compatibility of protective phenolic functionality was investigated with the implementation of indium (III) triflate-catalyzed oxidative esterification using Oxone in methanol. A wide range of protective moieties was selected and subjected to Oxone-mediated oxidative esterification. For example, sulfonates were found to be sufficiently stable and inert whereas acetals were susceptible to reaction conditions. The details of this investigation are pro-vided.","PeriodicalId":12770,"journal":{"name":"Green and Sustainable Chemistry","volume":"54 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":"{\"title\":\"The Compatibility of Groups Used to Protect Phenolic Functionality during Oxone-Mediated Oxidative Esterification\",\"authors\":\"T. Mineno, Yukizi Suzuki, Tomoya Nobuta, Daiki Takano, Hisao Kansui\",\"doi\":\"10.4236/gsc.2022.124007\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Protecting groups often play an essential role in organic synthesis, particularly for multi-step synthesis or natural product total synthesis. Various protecting groups areavailable to mask the vulnerable functionality; phenolic hydroxy groups are noteworthy examples, but their stability differs when protected. Herein, the compatibility of protective phenolic functionality was investigated with the implementation of indium (III) triflate-catalyzed oxidative esterification using Oxone in methanol. A wide range of protective moieties was selected and subjected to Oxone-mediated oxidative esterification. For example, sulfonates were found to be sufficiently stable and inert whereas acetals were susceptible to reaction conditions. The details of this investigation are pro-vided.\",\"PeriodicalId\":12770,\"journal\":{\"name\":\"Green and Sustainable Chemistry\",\"volume\":\"54 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2022-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green and Sustainable Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.4236/gsc.2022.124007\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green and Sustainable Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.4236/gsc.2022.124007","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
The Compatibility of Groups Used to Protect Phenolic Functionality during Oxone-Mediated Oxidative Esterification
Protecting groups often play an essential role in organic synthesis, particularly for multi-step synthesis or natural product total synthesis. Various protecting groups areavailable to mask the vulnerable functionality; phenolic hydroxy groups are noteworthy examples, but their stability differs when protected. Herein, the compatibility of protective phenolic functionality was investigated with the implementation of indium (III) triflate-catalyzed oxidative esterification using Oxone in methanol. A wide range of protective moieties was selected and subjected to Oxone-mediated oxidative esterification. For example, sulfonates were found to be sufficiently stable and inert whereas acetals were susceptible to reaction conditions. The details of this investigation are pro-vided.