Citation: Longlong Xi, Liting Du, Zhuangzhi Shi. Nickel-catalyzed reductive cross-coupling of polyfluoroarenes with alkyl electrophiles by site-selective C–F bond activation[J]. Chinese Chemical Letters, ;2022, 33(9): 4287-4292. doi: 10.1016/j.cclet.2022.01.077 shu

Nickel-catalyzed reductive cross-coupling of polyfluoroarenes with alkyl electrophiles by site-selective C–F bond activation

Longlong Xi ^a ,
Liting Du ^b ,
Zhuangzhi Shi ^{a, *,}

a.
State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
b.
Advanced Analysis and Testing Center, Nanjing Forestry University, Nanjing 210037, China

shiz@nju.edu.cn

Received Date: 18 November 2021
Revised Date: 26 January 2022
Accepted Date: 27 January 2022
Available Online: 3 February 2022

Figures(8)

A nickel-catalyzed reductive cross-coupling reactions between polyfluoroarenes and alkyl electrophiles is reported to access substituted fluoroarenes through chelation-assisted C–F activation. Diverse primary and secondary alkyl (pseudo)halides can be employed to couple with polyfluoroarenes, showing excellent regioselectivity. Furthermore, the nickel-catalyzed asymmetric cross-coupling of polyfluoroarenes with racemic alkyl halides is preliminarily explored. In addition, the practicability of the title transformation is also demonstrated by total synthesis of losmapimod and an analog as key steps. The developed method exhibits many advantages, including economic catalytic systems, commercially available alkyl electrophiles, and lack of sensitive organometallic reagents.
- Polyfluoroarenes,
- Nickel,
- Alkylation,
- Cross-coupling,
- C-F activation
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