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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 8: 2328 - 2332

DOI: https://doi.org/10.6023/cjoc201902036

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

  • Deng Chao ,
  • Zhou Jiaolong ,
  • Liu Huakui ,
  • Wang Lijia ,
  • Tang Yong
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  • 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 date: 2019-02-28

  Revised date: 2019-04-12

  Online published: 2020-05-08

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Abstract

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.

Cite this article

Deng Chao , Zhou Jiaolong , Liu Huakui , Wang Lijia , Tang Yong . Rh2(OAc)4 Catalyzed Wittig-Type Olefination: A Facile Access to Alkylidene and Arylidene Malonates[J]. Chinese Journal of Organic Chemistry, 2019 , 39(8) : 2328 -2332 . DOI: 10.6023/cjoc201902036

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