Citation: Qiao Li, Minjie Liu, Meifen Jiang, Li Wan, Yingtang Ning, Fen-Er Chen. Photo-induced 1,2-aryl migration of 2-chloro-1-arylpropanone under batch and flow conditions: Rapid, scalable and sustainable approach to 2-arylpropionic acids[J]. Chinese Chemical Letters, ;2024, 35(2): 108576. doi: 10.1016/j.cclet.2023.108576 shu

Photo-induced 1,2-aryl migration of 2-chloro-1-arylpropanone under batch and flow conditions: Rapid, scalable and sustainable approach to 2-arylpropionic acids

Qiao Li ^{a, b, c, d, 1} ,
Minjie Liu ^{b, c, 1} ,
Meifen Jiang ^{b, c} ,
Li Wan ^{b, c} ,
Yingtang Ning ^{b, c, *,} ,
Fen-Er Chen ^{a, b, c, d, *,}

a.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
b.
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai 200433, China
c.
Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai 200433, China
d.
Institute of Pharmaceutical Science and Technology, Zhejiang University of Technology, Hangzhou 310014, China

ningyt@fudan.edu.cn

rfchen@fudan.edu.cn

Received Date: 24 March 2023
Revised Date: 3 May 2023
Accepted Date: 15 May 2023
Available Online: 20 May 2023

Figures(4)

We report the photo-mediated 1,2-aryl migration of 2–chloro-1-arylpropanones to 2-arylpropionic acids using HCOONa as an acid scavenger. This pragmatically focused study obviates the multiple-step sequence in the industrially employed, ZnO-promoted rearrangement strategy, and offers rapid access to various 2-arylpropionic acids under environmentally friendly conditions. Furthermore, the successful transfer of this batch photochemistry to a continuous flow platform led to improved scalability and enabled the gram-scale synthesis of loxoprofen.
- Green chemistry,
- Flow chemistry,
- 2-Arylpropionic acids,
- Photo-Favorskii reaction
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