{"title":"Metal‐free visible‐light‐induced direct synthesis of alkyl‐substituted phosphonodithioates from white phosphorus (P4)","authors":"Fengxiao Wang, Xiyuan Zhang, Jiaming Xu, Qitao Shen, Bo Jiang, Zhiwei Miao","doi":"10.1002/adsc.202401355","DOIUrl":null,"url":null,"abstract":"The direct synthesis of organic phosphorus compounds from white phosphorus (P4) is a longstanding challenge in organic synthesis. Here, we present a novel visible light‐induced three‐component functionalization reaction that integrates P4, disulfide compounds, and N‐hydroxyphthalimide (NHPI) esters to produce alkyl‐substituted phosphonodithioates in a one‐pot process. Using 2,4,5,6‐tetrakis(carbazol‐9‐yl)‐1,3‐dicyanobenzene (4CzIPN) as a photocatalyst, blue LEDs (456 nm) as the light source, and N,N‐diisopropylethylamine (DIPEA) as the reducing agent in an acetone‐toluene solvent system, this method achieves moderate to good yields of structurally diverse phosphonodithioates. The reaction proceeds under mild conditions, ensures complete conversion of P4, avoids chlorination, and uses inexpensive, readily available starting materials, offering potential for large‐scale applications.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"221 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-12-07","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.202401355","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
The direct synthesis of organic phosphorus compounds from white phosphorus (P4) is a longstanding challenge in organic synthesis. Here, we present a novel visible light‐induced three‐component functionalization reaction that integrates P4, disulfide compounds, and N‐hydroxyphthalimide (NHPI) esters to produce alkyl‐substituted phosphonodithioates in a one‐pot process. Using 2,4,5,6‐tetrakis(carbazol‐9‐yl)‐1,3‐dicyanobenzene (4CzIPN) as a photocatalyst, blue LEDs (456 nm) as the light source, and N,N‐diisopropylethylamine (DIPEA) as the reducing agent in an acetone‐toluene solvent system, this method achieves moderate to good yields of structurally diverse phosphonodithioates. The reaction proceeds under mild conditions, ensures complete conversion of P4, avoids chlorination, and uses inexpensive, readily available starting materials, offering potential for large‐scale applications.
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.