Mechanism of photocatalyzed imine conversion: a relay process of sequential energy transfer, single electron transfer and proton transfer

Shuangshuang Ji, Jianfeng Sheng, Shang Gao, Zhipeng Pei, Fuming Ying, Jinshuai Song, Yanyan Zhu

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The use of imine compounds to generate alkyl radicals has been a topic of interest among synthetic chemists. However, the mechanism behind this conversion has yet to be fully understood. To shed light on this, a recent study utilized density functional theory calculations to investigate the mechanisms of photocatalyzed imidoyl radical formation and conversion. The study found that a sequential energy transfer, single electron transfer, and proton transfer pathway was energetically favorable for imidoyl radical generation. Interestingly, another substrate lacking 2,4,6-trimethoxy substituents exhibited poor reactivity due to its weak reduction ability and acidity, both in the ground state and photo-excited state.

Original languageEnglish
Pages (from-to)4565-4572
Number of pages8
JournalOrganic Chemistry Frontiers
Volume10
Issue number18
Early online date28 Jul 2023
DOIs
Publication statusPublished - 28 Jul 2023

Keywords

  • Imines
  • alkyl radicals
  • photocatalyzed imidoyl radicals

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