- Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
-
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.
- Lam, Long Yin,Ma, Cong
-
supporting information
p. 6164 - 6168
(2021/08/16)
-
- A Robust Pd-Catalyzed C-S Cross-Coupling Process Enabled by Ball-Milling
-
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.
- Browne, Duncan L.,Jones, Andrew C.,Nicholson, William I.,Smallman, Harry R.
-
supporting information
p. 7433 - 7438
(2020/10/09)
-
- DABCO-promoted Diaryl Thioether Formation by Metal-catalyzed Coupling of Sodium Sulfinates and Aryl Iodides
-
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.).
- Liu, Yanpeng,Lam, Long Yin,Ye, Jiqing,Blanchard, Nicolas,Ma, Cong
-
supporting information
p. 2326 - 2331
(2020/05/05)
-
- Exploration of the mechanism and scope of the CuI/DABCO catalysed C–S coupling reaction
-
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.
- Thomas, Anns Maria,Sherin,Asha, Sujatha,Manojkumar,Anilkumar, Gopinathan
-
supporting information
(2019/12/26)
-
- A general and inexpensive protocol for the Cu-catalyzed C-S cross-coupling reaction between aryl halides and thiols
-
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.
- Thomas, Anns Maria,Asha, Sujatha,Sindhu,Anilkumar, Gopinathan
-
supporting information
p. 6560 - 6564
(2015/11/09)
-
- 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
-
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.
- Swapna, Kokkirala,Murthy, Sabbavarapu Narayana,Jyothi, Mocharla Tarani,Nageswar, Yadavalli Venkata Durga
-
experimental part
p. 5989 - 5996
(2011/10/08)
-
- Microwave efficient S-arylation of thiols with aryl iodides using supported metal nanoparticles
-
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.
- Gonzalez-Arellano, Camino,Luque, Rafael,MacQuarrie, Duncan J.
-
experimental part
p. 1410 - 1412
(2009/07/10)
-
- POLY-N-HETEROCYCLIC CARBENE TRANSITION METAL COMPLEXES AND N-HETEROCYCLIC CARBENE TRANSITION METAL COMPLEXES FOR CARBON-SULFUR AND CARBON-OXYGEN COUPLING REACTIONS
-
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.
- -
-
Page/Page column 30-32
(2009/01/20)
-
- L-proline-promoted CuI-catalyzed C-S bond formation between aryl iodides and thiols
-
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.
- Zhang, Hui,Cao, Weiguo,Ma, Dawei
-
-
- The first N-heterocyclic carbene-based nickel catalyst for C-S coupling
-
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.
- Yugen, Zhang,Kao, Chin Ngeow,Ying, Jackie Y.
-
p. 3495 - 3498
(2008/02/12)
-
- Copper-carbene complexes and their use
-
The invention relates to copper-carbene complexes, to a process for preparing them and to their use in catalytic coupling reactions.
- -
-
Page/Page column 6
(2010/02/08)
-
- A CONVENIENT SRN1 SYNTHESIS OF AROMATIC NITRILES FROM DIAZONIUM SALTS VIA DIAZOSULFIDES
-
Properly substituted diazosulfides XC6H4-N=N-SPh (1) (either isolated or generated in situ from arenediazonium tetrafluoroborates and sodium benzenethiolate) react with tetrabutylammonium cyanide, in Me2SO under photon or electron stimulation, leading to nitriles XC6H4CN (2).Satisfactory yields of 2, comparable with those of the Sandmeyer reaction, are obtained when X= 3- or 4-CF3, 2-, 3-, or 4-CN, 4-F, 4-MeCO, 3-MeO, 4-NO2, 4-PhCO, and 4-PhSO2.For different reasons, the reaction practically fails as a useful nitrile synthesis when X= H, 4-MeO, 2-, or 3-NO2.The collected evidences agree well with the intervention of an SRN1 mechanism to which diazosulfides 1, given their easy reducibility followed by a prompt fragmentation of the C-N and N-S bonds, are convenient participating substrates.An important consequence of the mechanism involved is the behaviour of bromo and chloro derivatives (1: X= Br, Cl) which lead, through the contemporaneous introduction of two cyano functionalities, to more than satisfactory yields of the corresponding dicyanobenzenes.
- Petrillo, Giovanni,Novi, Marino,Garbarino, Giacomo,Dell'erba, Carlo
-
p. 4625 - 4634
(2007/10/02)
-
- BIS(ARENE)METAL COMPOUNDS I. NUCLEOPHILIC SUBSTITUTION OF BIS(η6-CHLOROBENZOTRIFLUORIDE)CHROMIUM(0) WITH THIOPHENOXIDE
-
The ortho, meta and para complexes of bis(η6-chlorobenzotrifluoride)chromium(0) were made by metal-vapor synthesis.Nucleophilic substitutions by thiophenoxide of these complexes are compared to nucleophilic substitutions by thiophenoxide on the uncoordinated arenes.It was found that substitution at the chloro position is more facile on the complexes than on the free arenes.Substitution of the chloro on the meta-isomer sandwich was more facile than substitution of the chloro on the ortho-isomer sandwich, contrary to the observed reactivity pattern in the free arenes.
- Harris, Ronald L.
-
p. 105 - 110
(2007/10/02)
-