108697-88-7Relevant articles and documents
DABCO-promoted Diaryl Thioether Formation by Metal-catalyzed Coupling of Sodium Sulfinates and Aryl Iodides
Liu, Yanpeng,Lam, Long Yin,Ye, Jiqing,Blanchard, Nicolas,Ma, Cong
, p. 2326 - 2331 (2020)
A scalable catalytic synthesis method using commodity chemicals for constructing diaryl thioethers directly from sodium arylsulfinates and iodoarenes is reported in this study. In the presence of CuO or other copper salts such as Cu(OAc)2 as well as palladium catalysts, DABCO demonstrated to be essential to promote this transformation. Various iodoarenes and aryl sulfinates were examined and demonstrated the viability of this method. The mechanistic study showed that radical reactions occurred, while DABCO N-oxide radical can be observed by mass spectrometry. A plausible catalytic mechanism involving DABCO is also discussed, suggesting synergistic reduction of sulfinate by Cu(II) and DABCO is the key step of this coupling reaction. (Figure presented.).
Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity
Sikari, Rina,Sinha, Suman,Das, Siuli,Saha, Anannya,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
, p. 4072 - 4085 (2019/04/01)
A simple and efficient approach of C-S cross-coupling of a wide variety of (hetero)aryl thiols and (hetero)aryl halides under mild conditions, mostly at room temperature, catalyzed by well-defined singlet diradical Ni(II) catalysts bearing redox noninnocent ligands is reported. Taking advantage of ligand centered redox events, the high-energetic Ni(0)/Ni(II) or Ni(I)/Ni(III) redox steps were avoided in the catalytic cycle. The cooperative participation of both nickel and the coordinated ligands during oxidative addition/reductive elimination steps allowed us to perform the catalytic reactions under mild conditions.
Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling
Guan, Pei,Cao, Changsheng,Liu, Yun,Li, Yunfei,He, Pan,Chen, Qian,Liu, Gang,Shi, Yanhui
supporting information, p. 5987 - 5992,6 (2012/12/12)
The cross-coupling reaction of aryl halides with aliphatic and aromatic thiols catalyzed by readily available Ni(OAc)2 with N-heterocyclic carbene (NHC) is reported. Ni(OAc)2/NHC catalyst showed good activities toward various aryl halides in C-S coupling reaction, even with aryl chlorides. Reactions occurred in excellent yields, broad scope, and high tolerance of functional groups.