Citation: Xuan Maojie, Lu Chunlei, Lin Bo-Lin. C-S coupling with nitro group as leaving group via simple inorganic salt catalysis[J]. Chinese Chemical Letters, ;2020, 31(1): 84-90. doi: 10.1016/j.cclet.2019.07.012 shu

C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

a.
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China
b.
School of Physical Science and Technology (SPST), ShanghaiTech University, Shanghai 201210, China

Received Date: 29 April 2019
Revised Date: 24 June 2019
Accepted Date: 4 July 2019
Available Online: 4 January 2019

Figures(4)

An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (S_NAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step additionelimination mechanism.
- Inorganic-salt catalysis,
- Nucleophilic aromatic substitution,
- C-S bond,
- Denitrification coupling,
- Kinetic isotope effect,
- Meisenheimer complex
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