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DOI: https://doi.org/10.6023/cjoc202506009

ARTICLE

Nickel/Photoredox Dual-Catalyzed C-O Bond Coupling Reactions of Aryl Bromides with Alcohols

  • Gao Shan ,
  • Xie Xin ,
  • Liu Yuanhong
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  • aHenan Institute of Advanced Technology, Zhengzhou University, Zhengzhou, 450001;
    bState Key Laboratory of Organometallic Chemistry, Shanghai Inistitute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, Shanghai, 200032

Received date: 2025-06-05

  Revised date: 2025-07-24

  Online published: 2025-08-27

Supported by

Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB0610000),the High-level Talent Research Start-up Project Funding of Henan Academy of Sciences (No. 242002063)

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Abstract

A nickel/photoredox dual-catalyzed C-O bond coupling reaction between aryl/heteroaryl bromides and alcohols has been developed. Alkyl aryl ethers were efficiently synthesized by using organic photoredox-catalyst 4CzIPN or 4DPAIPN in the presence of NiBr2·DME, a ligand, and a base under 456 nm blue LED irradiation at room temperature. The reaction likely involves the oxidative addition of Ni(0) intermediate to aryl bromide, ligand exchange with the alcohol, oxidization of the resulting Ni(II) intermediate by the excited photoredox catalyst to form Ni(III) intermediate, and subsequent reductive elimination. This method exhibits broad substrate scope of alcohols, including benzyl alcohols, primary alcohols, and secondary alcohols, and with remarkable functional group tolerance.

Key words： nickel-catalysis; photoredox; C-O bond coupling; alkyl aryl ethers

Cite this article

Gao Shan , Xie Xin , Liu Yuanhong . Nickel/Photoredox Dual-Catalyzed C-O Bond Coupling Reactions of Aryl Bromides with Alcohols[J]. Chinese Journal of Organic Chemistry, 0 : 10 -10 . DOI: 10.6023/cjoc202506009

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