2715-07-3Relevant articles and documents
Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
Lam, Long Yin,Ma, Cong
supporting information, p. 6164 - 6168 (2021/08/16)
A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.
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
supporting information, p. 2326 - 2331 (2020/05/05)
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.).
Exploration of the mechanism and scope of the CuI/DABCO catalysed C–S coupling reaction
Thomas, Anns Maria,Sherin,Asha, Sujatha,Manojkumar,Anilkumar, Gopinathan
supporting information, (2019/12/26)
A cost effective and easily available CuI/DABCO catalytic system has been developed for the C–S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides, providing excellent yields and good chemoselectivity. We have also explored the mechanism of the reaction using DFT studies.
A Robust Pd-Catalyzed C-S Cross-Coupling Process Enabled by Ball-Milling
Browne, Duncan L.,Jones, Andrew C.,Nicholson, William I.,Smallman, Harry R.
supporting information, p. 7433 - 7438 (2020/10/09)
An operationally simple mechanochemical C-S coupling of aryl halides with thiols has been developed. The reaction process operates under benchtop conditions without the requirement for a (dry) solvent, an inert atmosphere, or catalyst preactivation. The reaction is finished within 3 h. The reaction is demonstrated across a broad range of substrates; the inclusion of zinc metal has been found to be critical in some instances, especially for coupling of alkyl thiols.
A general and inexpensive protocol for the Cu-catalyzed C-S cross-coupling reaction between aryl halides and thiols
Thomas, Anns Maria,Asha, Sujatha,Sindhu,Anilkumar, Gopinathan
supporting information, p. 6560 - 6564 (2015/11/09)
A cost effective and easily available CuI/DABCO catalytic system has been developed for C-S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides providing excellent yields and good chemoselectivity.
Nano-CuFe2O4 as a magnetically separable and reusable catalyst for the synthesis of diaryl/aryl alkyl sulfides via cross-coupling process under ligand-free conditions
Swapna, Kokkirala,Murthy, Sabbavarapu Narayana,Jyothi, Mocharla Tarani,Nageswar, Yadavalli Venkata Durga
experimental part, p. 5989 - 5996 (2011/10/08)
An efficient protocol was developed for the CuFe2O4 nanopowder-catalyzed aryl-sulfur bond formation between aryl halide and thiol/disulfide. A variety of aryl sulfides were synthesized in impressive yields with good chemoselectivity and functional group tolerance in the presence of a catalytic amount of CuFe2O4, Cs2CO 3 as base, in nitrogen atmosphere, under ligand-free conditions, in DMSO as solvent at 100 °C. The catalyst is air-stable, inexpensive, magnetically separable and recyclable up to four cycles.
Microwave efficient S-arylation of thiols with aryl iodides using supported metal nanoparticles
Gonzalez-Arellano, Camino,Luque, Rafael,MacQuarrie, Duncan J.
experimental part, p. 1410 - 1412 (2009/07/10)
An efficient and green microwave-assisted heterogeneous S-arylation protocol, reported for the first time, provided excellent coupling conversions and selectivities in minutes of reaction using Fe (homocoupling) and Cu (cross-coupling) supported metal nanoparticles.
POLY-N-HETEROCYCLIC CARBENE TRANSITION METAL COMPLEXES AND N-HETEROCYCLIC CARBENE TRANSITION METAL COMPLEXES FOR CARBON-SULFUR AND CARBON-OXYGEN COUPLING REACTIONS
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Page/Page column 30-32, (2009/01/20)
Methods for carbon-sulfur (C S) or carbon-oxygen (C-O) coupling reactions are provided. The methods involve the use of a transition metal complex comprising a heterocyclic carbene ligand complexed with a transition metal. Transition metal complexes comprising a heterocyclic carbene ligand complexed with nickel are also provided. The nickel heterocylic carbene complexes may be used for C-S or C-O coupling reactions.
L-proline-promoted CuI-catalyzed C-S bond formation between aryl iodides and thiols
Zhang, Hui,Cao, Weiguo,Ma, Dawei
, p. 25 - 35 (2007/10/03)
An improved, mild procedure for the CuI-catalyzed coupling reactions of aryl iodides with aliphatic and aromatic thiols, using L-proline as the ligand, is reported. This procedure is noteworthy given its high generality and exceptional level of functional group toleration. Copyright Taylor & Francis Group, LLC.
The first N-heterocyclic carbene-based nickel catalyst for C-S coupling
Yugen, Zhang,Kao, Chin Ngeow,Ying, Jackie Y.
, p. 3495 - 3498 (2008/02/12)
We have developed the first N-heterocyclic carbene (NHC)-based transition metal catalysts for C-S coupling reactions. Ni-NHC catalysts showed good to excellent activities toward various aryl halides in C-S coupling reactions. The catalytic activities were greatly affected by the electronic and steric properties of the NHC ligands. The new catalysts were inexpensive, easy to synthesize, and environmentally friendly. They could be excellent candidates to replace Pd-organophosphanes for C-S coupling catalysis.
