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Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 1: 212 - 219

DOI: https://doi.org/10.6023/cjoc202406008

ARTICLES

Application of Triborylmethane Reagent in the Stereoselective Synthesis of Dissymmetric gem-Diborylalkenes

  • Tiantian Yang ,
  • Du Chen ,
  • Peng Zhang ,
  • Chao Liu
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  • a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
    b University of Chinese Academy of Sciences, Beijing 100049
*E-mail: ;

Received date: 2024-06-07

  Revised date: 2024-08-11

  Online published: 2024-09-27

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Abstract

A novel triborylmethane reagent was successfully synthesized, which reacted with aldehydes under the condition of pentamethyldiethylenetriamine (PMDETA) as additive, enabling the synthesis of dissymmetrical gem-diborylalkenes. The method exhibits excellent stereoselectivity and good yields. The reaction has good substrate compatibility and the two boryl moieties in the product have different reactivities. Through cross-coupling with aryl halides, the Bpin moiety can be converted into an aryl group, achieving the stereoselective synthesis of trisubstituted vinylboronates.

Key words： gem-diborylalkenes; B—O elimination; boron reagent; aldehydes

Cite this article

Tiantian Yang , Du Chen , Peng Zhang , Chao Liu . Application of Triborylmethane Reagent in the Stereoselective Synthesis of Dissymmetric gem-Diborylalkenes[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 212 -219 . DOI: 10.6023/cjoc202406008

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