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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 7: 2676 - 2683

DOI: https://doi.org/10.6023/cjoc202102039

ARTICLES

Sodium Iodide-Triphenylphosphine-Mediated Photoredox Alkylation of Aldimines

  • Ziyan Shao ,
  • Qingli Zhou ,
  • Jiancheng Wang ,
  • Rui Tang ,
  • Yuehai Shen
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  • Center for Pharmaceutical Sciences and Engineering, Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500
* Corresponding author. E-mail:

Received date: 2021-02-22

  Revised date: 2021-04-02

  Online published: 2021-04-29

Supported by

National Natural Science Foundation of China(21662022); Ronald J Quinn AM Academician Workstation and the Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province(2019IC003)

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Abstract

The photoredox reactions involving electron donor-acceptor (EDA) complexes have attracted significant attentions in the last decade. Very recently, the sodium iodide-triphenylphosphine-N-acyloxyphthalimide EDA complex has been discovered and employed in developing several net redox-neutral photoreactions. Herein, the EDA complex has been applied in a net reductive setup for the first time to establish a photoredox alkylation of aldimines without photosensitizer. The reaction affords not only high yields for secondary, tertiary andα-heterosubstituted alkyl radicals, but also high yields for primary alkyl radicals, and moderate to high yields for electron-rich or secondary benzylic radicals, two difficult groups of radicals in previous studies. This work provides an efficient and reliable approach for the synthesis of unnatural amino acids and amines.

Key words： photoredox; aldimine; electron donor-acceptor complex

Cite this article

Ziyan Shao , Qingli Zhou , Jiancheng Wang , Rui Tang , Yuehai Shen . Sodium Iodide-Triphenylphosphine-Mediated Photoredox Alkylation of Aldimines[J]. Chinese Journal of Organic Chemistry, 2021 , 41(7) : 2676 -2683 . DOI: 10.6023/cjoc202102039

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