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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 5: 1808 - 1814

DOI: https://doi.org/10.6023/cjoc202301027

ARTICLES

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

  • Zhicheng Bao ,
  • Muyao Li ,
  • Jianbo Wang
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  • Beijing National Laboratory of Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871
* Corresponding author. E-mail:

Received date: 2023-01-31

  Revised date: 2023-03-12

  Online published: 2023-03-24

Supported by

National Natural Science Foundation of China(21871010)

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Abstract

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

Cite this article

Zhicheng Bao , Muyao Li , Jianbo Wang . Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane[J]. Chinese Journal of Organic Chemistry, 2023 , 43(5) : 1808 -1814 . DOI: 10.6023/cjoc202301027

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