Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (8): 2328-2332.DOI: 10.6023/cjoc201902036 Previous Articles     Next Articles


Rh2(OAc)4催化的Wittig-Type烯基化反应: 一种合成烷基、芳基取代的亚烷基丙二酸酯的简便方法

邓超†,a,b, 周姣龙†,*,a, 刘华魁a, 王丽佳*,c, 唐勇a   

  1. a中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032
    b南京农业大学理学院 江苏省农药学重点实验室 南京 210095
    c华东师范大学化学与分子工程学院 上海 200241
  • 收稿日期:2019-02-28 修回日期:2019-04-12 发布日期:2020-05-08

Rh2(OAc)4 Catalyzed Wittig-Type Olefination: A Facile Access to Alkylidene and Arylidene Malonates

Deng Chao†,a,b, Zhou Jiaolong†,*,a, Liu Huakuia, Wang Lijia*,c, Tang Yonga   

  1. aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    bJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095
    cSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241
  • Received:2019-02-28 Revised:2019-04-12 Published:2020-05-08
  • Contact: * E-mail:;

In the presence of triphenylarsine and catalytic amount of Rh2(OAc)4, one pot reactions with carbonyl compounds and dimethyl diazomalonate give the corresponding alkylidene and arylidene malonates in moderate to excellent yields (59%~99%). The scope of the carbonyl compounds covered a broad range, including aromatic and aliphatic aldehydes and ketone. The reaction was easily scaled up to gram scale with 0.5 mol% rhodium catalyst loading. The preliminary mechanistic studies showed that the olefination proceeded via a rhodium-carbene transformed arsonium ylide pathway.