Transition metal-free photocatalytic reductive deuteration of ketone derivatives  

作　　者：Jiaxin Cai Yanjun Li Ziqi Ye Wenqian Wang Yu Mei Lin Lei Gong 

机构地区：[1]Key Laboratory of Chemical Biology of Fujian Province,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China [2]Innovation Laboratory for Sciences and Technologies of Energy Materials of Fujian Province(IKKEM),Xiamen 361005,China

出　　处：《Green Synthesis and Catalysis》2023年第3期253-257,共5页绿色合成与催化（英文）

基　　金：support from the National Natural Science Foundation of China(Nos.22071209 and 22071206);the national youth talent support program,and the Fundamental Research Funds for the Central Universities(No.20720190048).

摘　　要：Deuterium labelling techniques have shown widespread applications in organic synthesis,analytic chemistry,life science and material science.The design of practical deuteration reactions which is environmentally friendly is highly desired for pharmaceutical development and industrial processes while remaining underexplored.We herein report a convenient,transition metal-free strategy for reductive deuteration of ketone derivatives toα-deuterated alcohols by employing a conjugated aryl amine-based organophotocatalyst,a dipropyl disulfide cocatalyst and an inorganic reductant.Upon irradiation with visible light and under an air atmosphere,a variety of diaryl ketones,heteroaryl ketones,cyclic ketones,α-ketoesters,benzil derivatives,aliphatic ketones and drug-like molecules were converted into correspondingα-deuterated aryl alcohols in good to excellent yields and with high deuterium incorporation(up to 99%D-incorporation).Only low toxic side-products,such as sodium salts and carbon dioxide,were generated.Consequently,the synthetic utility of this method is highlighted by the preparation of several D-labeled drug-like molecules,including orphenadrine,carbinoxamine and modafinil.

关 键 词：DEUTERATION PHOTOREDOX ORGANOCATALYSIS Visible light α-Deuterated alcohols 

分 类 号：O644.1[理学—物理化学]