Organoboron Reagent-Controlled Selective (Deutero)Hydrodefluorination
Zheng-Jia Shen
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Chen Zhu
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
These authors contributed equally to this work.
Search for more papers by this authorXiao Zhang
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
Search for more papers by this authorProf. Dr. Chao Yang
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Magnus Rueping
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
Search for more papers by this authorCorresponding Author
Prof. Dr. Lin Guo
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wujiong Xia
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorZheng-Jia Shen
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Chen Zhu
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
These authors contributed equally to this work.
Search for more papers by this authorXiao Zhang
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
Search for more papers by this authorProf. Dr. Chao Yang
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Magnus Rueping
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900 Saudi Arabia
Search for more papers by this authorCorresponding Author
Prof. Dr. Lin Guo
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wujiong Xia
State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen, 518055 China
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorAbstract
(Deuterium-labeled) CF2H- and CFH2-moieties are of high interest in drug discovery. The high demand for the incorporation of these fluoroalkyl moieties into molecular structures has witnessed significant synthetic progress, particularly in the (deutero)hydrodefluorination of CF3-containing compounds. However, the controllable replacement of fluorine atoms while maintaining high chemoselectivity remains challenging. Herein, we describe the development of a selective (deutero)hydrodefluorination reaction via electrolysis. The reaction exhibits a remarkable chemoselectivity control, which is enabled by the addition of different organoboron sources. The procedure is operationally simple and scalable, and provides access in one step to high-value building blocks for application in medicinal chemistry. Furthermore, density functional theory (DFT) calculations have been carried out to investigate the reaction mechanism and to rationalize the chemoselectivity observed.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
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