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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 5: 1857 - 1867

DOI: https://doi.org/10.6023/cjoc202212019

ARTICLES

Merging Electron Transfer Activation with 1,2-Metalate Migration: Deoxygenative Silylation of Amides

  • Wenhan Yang ,
  • Jiwen Jiao ,
  • Xiaoming Wang
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  • a College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032
    c School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024
* Corresponding author. E-mail:

Received date: 2022-12-14

  Revised date: 2023-02-01

  Online published: 2023-02-23

Supported by

National Natural Science Foundation of China(22171278); National Natural Science Foundation of China(21821002)

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Abstract

A direct deoxygenative silylation of amides with silylboronate reagents is developed in the presence of SmI2/Mg, affording a variety of high value-added α-aminosilane compounds in moderate to excellent yields with good functional group compatibility. The key to the success of this strategy lies in the merging of activation of amides induced by electron transfer with 1,2-metalate migration. The addition of Xantphos ligand can improve the reaction efficiency. The reactions are operationally simple and proceed under mild conditions, the raw materials are easily available and the products are highly valuable.

Key words： amide; electron transfer; silylboronate reagent; 1,2-metalate migration; α-aminosilane

Cite this article

Wenhan Yang , Jiwen Jiao , Xiaoming Wang . Merging Electron Transfer Activation with 1,2-Metalate Migration: Deoxygenative Silylation of Amides[J]. Chinese Journal of Organic Chemistry, 2023 , 43(5) : 1857 -1867 . DOI: 10.6023/cjoc202212019

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