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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 4: 1510 - 1516

DOI: https://doi.org/10.6023/cjoc202210005

ARTICLES

A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene

  • Xinyu Zhang ,
  • Huihui Geng ,
  • Shilei Zhang ,
  • Wei Wang ,
  • Xiaobei Chen
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  • Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, and State Key Laboratory of Bioengineering Reactor, School of Pharmacy, East China University of Science & Technology, Shanghai 200237
* Corresponding author. ;

Received date: 2022-10-06

  Revised date: 2022-11-20

  Online published: 2022-12-12

Supported by

National Natural Science Foundation of China(22071053); National Natural Science Foundation of China(22271206); Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism(grant 2021 Sci & Tech 03-28); Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD); Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism(Shanghai Municipal Education Commission)

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Abstract

An efficient method has been developed for the synthesis of deuterated benzoins from two molecules of aldehydes under the catalysis of N-heterocyclic carbene by using D2O as the deuterium source, providing the products with deuterium selectively incorporated at the α-position of ketone group. The method features simple operation and mild reaction conditions, and a variety of aromatic aldehyde substrates could afford products with high deuterium incorporation.

Key words： deuteration; deuteroxide; benzoin condensation; N-heterocyclic carbene; organocatalysis

Cite this article

Xinyu Zhang , Huihui Geng , Shilei Zhang , Wei Wang , Xiaobei Chen . A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene[J]. Chinese Journal of Organic Chemistry, 2023 , 43(4) : 1510 -1516 . DOI: 10.6023/cjoc202210005

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