Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1706-1712.DOI: 10.6023/cjoc202303025 Previous Articles     Next Articles

Special Issue: 有机硼化学专辑



陈志豪a, 范奇b, 尹标林b, 李清江a, 王洪根a,*()   

  1. a 中山大学药学院 广东省手性分子与药物发现重点实验室 广州 510006
    b 华南理工大学化学与化工学院 广东省功能分子工程重点实验室 广州 510640
  • 收稿日期:2023-03-17 修回日期:2023-04-14 发布日期:2023-04-26
  • 通讯作者: 王洪根
  • 基金资助:
    国家自然科学基金(22022114); 国家自然科学基金(21971261); 广东省基础与应用基础研究基金联合基金(2020A1515010624); 广东珠江人才计划本土创新科研团队项目基金(2017BT01Y093)

Progress in the Syntheses of α-Boryl Carbonyl Compounds

Zhihao Chena, Qi Fanb, Biaolin Yinb, Qingjiang Lia, Honggen Wanga()   

  1. a Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006
    b Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640
  • Received:2023-03-17 Revised:2023-04-14 Published:2023-04-26
  • Contact: Honggen Wang
  • Supported by:
    National Natural Science Foundation of China(22022114); National Natural Science Foundation of China(21971261); Guangdong Basic and Applied Basic Research Foun- dation(2020A1515010624); Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program(2017BT01Y093)

α-Boryl carbonyl compounds have traditionally been considered thermodynamically unstable and prone to undergo 1,3-boron migration. In recent years, with the development and understanding of sp3-hybridized boron or tetra-coordinated boron, methods for synthesizing stable and separable α-boryl carbonyl compounds have been actively developed. These methods include the insertion reaction of borane with diazo esters, sulfur ylides and other carbene precursors, the free-radical borylation reaction of α,β-unsaturated carbonyl compounds, and late-stage structural modification reactions of boron-contain- ing compounds. The recent advances in the synthesis of α-boryl carbonyl compounds are reviewed based on different reaction types, and the existing challenges and future research directions are discussed.

Key words: carbene precursor, insertion reaction of borane, radical borylation reaction, α,β-unsaturated carbonyl compound, boronate, functionalized alkyne