{"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}
引用次数: 0
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.
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。
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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