Citation: Yu-Zhong Yang, Gui-Fen Lv, Ming Hu, Yang Li, Jin-Heng Li. Nickel-catalyzed umpolung C–S radical reductive cross coupling of S-(trifluoromethyl)arylsulfonothioates with alkyl halides[J]. Chinese Chemical Letters, ;2023, 34(11): 108590. doi: 10.1016/j.cclet.2023.108590 shu

Nickel-catalyzed umpolung C–S radical reductive cross coupling of S-(trifluoromethyl)arylsulfonothioates with alkyl halides

Yu-Zhong Yang ^a ,
Gui-Fen Lv ^a ,
Ming Hu ^{a, b} ,
Yang Li ^{a, *,} ,
Jin-Heng Li ^{a, b, c, d, *,}

a.
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China
b.
State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
c.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
d.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

^☆

liyang8825490@126.com

jhli@hnu.edu.cn

Received Date: 9 March 2023
Revised Date: 14 May 2023
Accepted Date: 18 May 2023
Available Online: 22 May 2023

Figures(5)

A new cooperative nickel reductive catalysis and N,N-dimethylformamide-mediated strategy for umpolung C–S radical reductive cross coupling of S-(trifluoromethyl)arylsulfonothioates with alkyl halides to produce alkyl aryl thioethers is described. This reaction features excellent selectivity, wide functionality tolerance, broad substrate scope, and facile late-stage modification of biologically relevant molecules. Mechanistic studies recognize initial generation of an amidyl radical anion via thermoinduced reduction of DMF with Sn, followed by umpolung reduction and single electron transfer of the nucleophilic sulfonyl moiety to form a sulphydryl radical and engage the Ni⁰/Ni^Ⅰ/Ni^Ⅲ/Ni^Ⅰ catalytic cycle.
- Nickel,
- Radical,
- Reductive cross coupling,
- S-(Trifluoromethyl)arylsulfonothioates,
- Alkyl halides,
- Alkyl aryl thioethers
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