{"title":"Cu-Catalyzed Formal Addition of Aliphatic C(sp3)−H Bonds to Alkenes via Phenyl Radical Involved Intermolecular HAT","authors":"Peizhi Bai, Xin Zhang, Qinshuang Su, Tiebo Xiao, Yubo Jiang, Guoying Zhang, Yinjun Xie, Guiping Qin","doi":"10.1002/adsc.202400377","DOIUrl":null,"url":null,"abstract":"<p>A copper catalyzed aerobic formal addition of aliphatic C(<i>sp</i>3)−H bonds to alkenes via a phenyl radical mediated intermolecular HAT process is reported herein, in which the phenylhydrazine not only acts as a HAT reagent precursor, but also as a hydrogen atom donor. This reaction affords an alternative method for the direct formal addition of aliphatic C(<i>sp</i>3)−H bonds to alkenes utilizing air as the radical initiator without additional reductants at ambient temperature. A variety of alkanes and electron-deficient alkenes are successfully incorporated, furnishing a series of aliphatic C(<i>sp</i>3)−H formal addition products in 20–93% yield. Preliminary mechanistic studies show that the 2-tetrahydrofuranyl and phenyl radical are formed in this reaction.</p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":4.4000,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/adsc.202400377","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 copper catalyzed aerobic formal addition of aliphatic C(sp3)−H bonds to alkenes via a phenyl radical mediated intermolecular HAT process is reported herein, in which the phenylhydrazine not only acts as a HAT reagent precursor, but also as a hydrogen atom donor. This reaction affords an alternative method for the direct formal addition of aliphatic C(sp3)−H bonds to alkenes utilizing air as the radical initiator without additional reductants at ambient temperature. A variety of alkanes and electron-deficient alkenes are successfully incorporated, furnishing a series of aliphatic C(sp3)−H formal addition products in 20–93% yield. Preliminary mechanistic studies show that the 2-tetrahydrofuranyl and phenyl radical are formed in this reaction.
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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