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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 5: 1852 - 1856

DOI: https://doi.org/10.6023/cjoc202212033

ARTICLES

Alkyl Exchange between Alkylsilanes and Hydroborenium Ion

  • Xi Wang ,
  • Zhen-Hua Li ,
  • Huadong Wang
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  • Department of Chemistry, Fudan University, Shanghai 200438
* Corresponding author. E-mail:

Received date: 2022-12-27

  Revised date: 2023-02-05

  Online published: 2023-02-23

Supported by

National Natural Science Foundation of China(21871051); National Natural Science Foundation of China(22071027); National Natural Science Foundation of China(22271050)

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Abstract

Ligand exchange between boron and silicon centers offers a convinient way for the synthesis of organoboron compounds. While such method is well-established for the preparation of arylboranes, examples of alkyl exchange between boron and silicon centers are very rare. Here, it was demonstrated that an N-heterocyclic carbene stablized hydroborenium ion readily reacts with alkylsilanes at ambient conditions to afford the corresponding alkylborenium complexes. Theoretical calculations suggest that the activation of Si—C(alkyl) bonds involves a σ-bond metathesis pathway.

Key words： boron; silicon; Si—C bond; σ-bond metathesis

Cite this article

Xi Wang , Zhen-Hua Li , Huadong Wang . Alkyl Exchange between Alkylsilanes and Hydroborenium Ion[J]. Chinese Journal of Organic Chemistry, 2023 , 43(5) : 1852 -1856 . DOI: 10.6023/cjoc202212033

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