Metallaphotoredox?Catalyzed O?Arylation of Serine北大核心CSCD

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. © 2022, Science Press (China). All rights reserved.

Metallaphotoredox?Catalyzed O?Arylation of Serine

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.