{"title":"光诱导的无过渡金属化学歧化磷酸化-烯烃的过氧化和氧化磷酸化反应","authors":"Jun Pan, Yuting Feng, Leiyang Lv, Zhiping Li","doi":"10.1002/adsc.202400606","DOIUrl":null,"url":null,"abstract":"A visible‐light‐promoted chemodivergent phosphorylation‐peroxidation and oxyphosphorylation of alkenes with phosphine oxides and HOOtBu was realized under transition‐metal‐free conditions. Using the commercially available Eosin Y as a SET‐photocatalyst, the β‐peroxy‐phosphine oxides were selectively obtained with a catalytic amount of base, while the addition of acid led to the exclusive formation of ꞵ‐keto‐phosphine oxides. Control experiments showed that Eosin Y could also act as a HAT‐catalyst to induce the O‐O bond cleavage of peroxides under acidic conditions.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":4.4000,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes\",\"authors\":\"Jun Pan, Yuting Feng, Leiyang Lv, Zhiping Li\",\"doi\":\"10.1002/adsc.202400606\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A visible‐light‐promoted chemodivergent phosphorylation‐peroxidation and oxyphosphorylation of alkenes with phosphine oxides and HOOtBu was realized under transition‐metal‐free conditions. Using the commercially available Eosin Y as a SET‐photocatalyst, the β‐peroxy‐phosphine oxides were selectively obtained with a catalytic amount of base, while the addition of acid led to the exclusive formation of ꞵ‐keto‐phosphine oxides. Control experiments showed that Eosin Y could also act as a HAT‐catalyst to induce the O‐O bond cleavage of peroxides under acidic conditions.\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2024-07-06\",\"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.202400606\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202400606","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
摘要
在无过渡金属的条件下,利用膦氧化物和 HOOtBu 实现了可见光促进的烯烃磷酸化-过氧化和氧磷酸化化学反应。使用市售的曙红 Y 作为 SET 光催化剂,在加入一定量的碱催化下,可选择性地获得 β-过氧膦氧化物,而加入酸则只能形成ꞵ-酮膦氧化物。对照实验表明,在酸性条件下,曙红 Y 也可以作为 HAT 催化剂诱导过氧化物的 O-O 键裂解。
Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes
A visible‐light‐promoted chemodivergent phosphorylation‐peroxidation and oxyphosphorylation of alkenes with phosphine oxides and HOOtBu was realized under transition‐metal‐free conditions. Using the commercially available Eosin Y as a SET‐photocatalyst, the β‐peroxy‐phosphine oxides were selectively obtained with a catalytic amount of base, while the addition of acid led to the exclusive formation of ꞵ‐keto‐phosphine oxides. Control experiments showed that Eosin Y could also act as a HAT‐catalyst to induce the O‐O bond cleavage of peroxides under acidic conditions.
期刊介绍:
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
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