Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1808-1814.DOI: 10.6023/cjoc202301027 Previous Articles     Next Articles

Special Issue: 有机硼化学专辑



鲍志成, 李慕尧, 王剑波*()   

  1. 北京大学化学与分子工程学院 北京分子科学国家研究中心 北京 100871
  • 收稿日期:2023-01-31 修回日期:2023-03-12 发布日期:2023-03-23
  • 通讯作者: 王剑波
  • 基金资助:

Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane

Zhicheng Bao, Muyao Li, Jianbo Wang()   

  1. Beijing National Laboratory of Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871
  • Received:2023-01-31 Revised:2023-03-12 Published:2023-03-23
  • Contact: Jianbo Wang
  • Supported by:
    National Natural Science Foundation of China(21871010)

The copper-catalyzed cross-coupling reaction of 1,1-bis[(pinacolato)boryl]methane with α-diazophenylacetate as carbene precursor was reported, leading to the construction of C(sp3)—C(sp3) bond. Reaction optimization experiments showed that Monophos ligand was critical for the success of this reaction. In situ oxidation afforded the corresponding primary alcohols instead of the relatively unstable boronates. The reaction has high efficiency and good functional group compatibility. The two-step transformation represents a formal hydroxymethylation of diazoacetates.

Key words: copper catalysis, C(sp3)—C(sp3) bond formation, diazo compounds, bis[(pinacolato)boryl]methane