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 ¹Minjie Liu ²Meifen Jiang ²Li Wan ²Yingtang Ning ²Fen-Er Chen¹

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作者信息

1. College of Chemical Engineering,Zhejiang University of Technology,Hangzhou 310014,China;Engineering Center of Catalysis and Synthesis for Chiral Molecules,Fudan University,Shanghai 200433,China;Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs,Shanghai 200433,China;Institute of Pharmaceutical Science and Technology,Zhejiang University of Technology,Hangzhou 310014,China
2. Engineering Center of Catalysis and Synthesis for Chiral Molecules,Fudan University,Shanghai 200433,China;Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs,Shanghai 200433,China
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Abstract

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.

Key words

Green chemistry/Flow chemistry/2-Arylpropionic acids/Photo-Favorskii reaction

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基金项目

国家自然科学基金(22077018)

出版年

2024

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCDCSCD

影响因子：0.771

ISSN：1001-8417

参考文献量51

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