Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (10): 1610-1616.DOI: 10.19894/j.issn.1000-0518.220066

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Metallaphotoredox⁃Catalyzed O⁃Arylation of Serine

Ying-Zi LI, Ting LIU, Si-Qi WU, Xuan FANG, Jing GAO, Shi TANG()   

  1. College of Chemistry and Chemical Engineering,Jishou University,Jishou 416000,China
  • Received:2022-03-11 Accepted:2022-07-07 Published:2022-10-01 Online:2022-10-05
  • Contact: Shi TANG
  • About
  • Supported by:
    the National Natural Science Foundation of China(21961011);the Graduate Research Project of the Science and Technology Department of Jishou University(15JDY001);the Hunan Graduate Training and Innovation Base Project of Jishou University(2014KFXM06)


A metallaphotoredox catalyzed hydroxyl aromatization of serine is developed to achieve rapid synthesis of aryl ethers of various serine derivatives. Under the catalytic system of ethylene glycol dimethyl ether nickel bromide (NiBr2(dme))/4,4'-dimethoxy-2,2'-bipyridine/zinc powder and synergistic iridium photoredox catalysis, nickel is catalyzed and inserted into the C—Br bond, and then followed by transmetalation with the hydroxyl group of serine. The resulting Ni(Ⅱ) species are oxidized by the excited Ir(Ⅲ) species to a Ni(Ⅲ) intermediate. This intermediate is unstable and reductive elimination takes place rapidly to give the target product O-arylated serine in the yields from 65% to 39%. Through a metallaphotoredox catalysis strategy, the reaction features mild, efficient, clean and broad scope of substrate, providing a new way for the synthesis of various serine derivatives with medicinal value.

Key words: Nickel photocatalysis, Cross coupling, Arylation reaction, Serine

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