Difluoromethylated Difunctionalization of Alkenes under Visible Light,The Journal of Organic Chemistry

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Difluoromethylated Difunctionalization of Alkenes under Visible Light
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-02-01 , DOI: 10.1021/acs.joc.3c02552
Yuping Zhu ₁ , Yan-Hua Qiu ₁ , Xiao-Kang Dai ₁ , Wenjun Luo ₁ , Xiangjun Peng ₂ , Zhengwang Chen ₁ , Daohong Yu ₁

Affiliation

Difluoromethylated compounds usually act as bioisosteres for alcohol functional groups and show unique physicochemical and biological properties. The cyano-difluoromethylation of alkenes using 5-((difluoromethyl)sulfonyl)-1-phenyl-1H-tetrazole as a CF₂H radical difluoromethyl precursor was developed to afford nitriles including a CF₂H group. A low-cost, stable, easily handled 5-((difluoromethyl)sulfonyl)-1-methyl-1H-tetrazole (DFSMT) was synthesized and applied as the radical CF₂H reagent. Using DFSMT as the radical CF₂H precursor, the oxyl-difluoromethylation of alkenes was developed to obtain difluoromethylated ether products. All of the reactions showed good functional group tolerability. Initial mechanistic experiments indicated that the CF₂H radical was involved as the key active intermediate.

中文翻译：

可见光下烯烃的二氟甲基化双官能化

二氟甲基化化合物通常充当醇官能团的生物等排体，并表现出独特的理化和生物学特性。使用5-((二氟甲基)磺酰基)-1-苯基-1H-四唑作为CF ₂ H自由基二氟甲基前体进行烯烃的氰基二氟甲基化，得到包含CF ₂ H基团的腈。合成了低成本、稳定、易于操作的5-((二氟甲基)磺酰基)-1-甲基-1H-四唑(DFSMT)，并将其用作自由基CF ₂ H试剂。使用DFSMT作为自由基CF ₂ H前体，开发了烯烃的氧基二氟甲基化反应以获得二氟甲基化醚产物。所有反应均表现出良好的官能团耐受性。初步的机理实验表明CF ₂ H自由基作为关键的活性中间体参与其中。

更新日期：2024-02-01

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