- Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction
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This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.
- Pan, Yi,Wang, Yang,Wang, Yi,Zhang, Feng
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- DABCO-promoted Diaryl Thioether Formation by Metal-catalyzed Coupling of Sodium Sulfinates and Aryl Iodides
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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
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supporting information
p. 2326 - 2331
(2020/05/05)
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- Modified conditions for copper-catalyzed ipso-thiolation of arylboronic acid esters with thiosulfonates
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An efficient ipso-thiolation of arylboronic acid esters with thiosulfonates has been achieved under mild and odorless conditions using a copper catalyst. The use of TMEDA and cesium fluoride as the ligand and base, respectively, dramatically facilitated the desired transformation. The method exhibited a broad substrate scope, which allowed for the expeditious synthesis of diverse aryl sulfides from easily available starting materials.
- Kanemoto, Kazuya,Yoshida, Suguru,Hosoya, Takamitsu
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supporting information
p. 85 - 88
(2018/01/26)
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- Nickel Phosphite/Phosphine-Catalyzed C-S Cross-Coupling of Aryl Chlorides and Thiols
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A method for the coupling of aryl chlorides and thiophenols using an air-stable nickel(0) catalyst is described. This thioetherification procedure can be effectively applied to a range of electronically diverse aryl/heteroaryl chlorides without more expensive metal catalysts such as palladium, iridium, or ruthenium. This investigation also illustrates both, a variety of thiol coupling partners and, in certain cases, the use of Cs2CO3.
- Jones, Kieran D.,Power, Dennis J.,Bierer, Donald,Gericke, Kersten M.,Stewart, Scott G.
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supporting information
p. 208 - 211
(2018/01/17)
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- Nano CoCuFe2O4-catalyzed coupling reaction of arylboronic acid with amines and thiols: An atom-economic and ligand-free route to access unsymmetrical amines and sulfides
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An efficient protocol was developed for the nano CoCuFe2O4-catalyzed C-N and C-S bond formation. By this catalytic system, both amine and sulfide-based structural motifs were formed efficiently in aryl halide-free route. The amination reaction of phenyl boronic acid with various types of amines was conducted under ligand-free conditions, in ethanol as a green solvent at 60°C. Unsymmetrical diaryl/aryl alkyl sulfide synthesis via the coupling reaction of arylboronic acids with thiols was also conducted. The nano cobalt-copper ferrite was used as a heterogenous efficient, inexpensive, magnetically separable and recyclable catalyst that can be used for several cycles.
- Moghaddam, Firouz Matloubi,Pourkaveh, Raheleh,Gholamtajari, Milad
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- CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chlorides
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We report a general copper-catalyzed cross-coupling of thiols with aryl halides by using N-aryl-N′-alkyl oxalic diamide (L3) or N,N′-dialkyl oxalic diamide (L5) as the ligand. Both aryl and alkyl thiols can be coupled with unactivated aryl bromides and chlorides to give the desired products in good yields. Furthermore, this system features a broad substrate scope and good tolerance of functional groups. Importantly, the oxalic diamides are stable and can be prepared easily from commercially available and cheap starting materials.
- Chen, Chia-Wei,Chen, Yi-Ling,Reddy, Daggula Mallikarjuna,Du, Kai,Li, Chao-En,Shih, Bo-Hao,Xue, Yung-Jing,Lee, Chin-Fa
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supporting information
p. 10087 - 10091
(2017/08/01)
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- Synthesis of o-Aryloxy Triarylsulfonium Salts via Aryne Insertion into Diaryl Sulfoxides
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The aryne insertion into "S-O" bond has been validated recently. This technology is elusively applied to the synthesis of thioethers. In contrast to the reported cases, the reaction described furnished o-aryloxy triarylsulfonium salts, in lieu of thioethe
- Li, Xiaojin,Sun, Yan,Huang, Xin,Zhang, Lei,Kong, Lichun,Peng, Bo
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supporting information
p. 838 - 841
(2017/02/26)
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- TBATB mediated debenzylative cross-coupling of aryl benzyl sulfides with electron rich compounds: Synthesis of diaryl sulfides
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An efficient TBATB mediated debenzylative cross coupling of aryl benzyl sulfides with electron rich compounds provides diaryl sulfides in moderate to excellent yield. The salient features of the present protocol are simplicity, high efficiency and compati
- Hazarika, Sukanya,Gogoi, Prasanta,Barman, Pranjit
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p. 25765 - 25767
(2015/10/20)
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- An efficient protocol for the carbon-sulfur cross-coupling of sulfenyl chlorides with arylboronic acids using a palladium catalyst
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An efficient protocol for carbon-sulfur bond formation is developed, which involves the cross-coupling of sulfenyl chlorides and arylboronic acids catalyzed by a novel palladium-Schiff base complex. Good to high product yields, short reaction times, and mild reaction conditions are important features of this new method. Georg Thieme Verlag Stuttgart · New York.
- Gogoi, Prasanta,Kalita, Mukul,Barman, Pranjit
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p. 866 - 870
(2014/04/03)
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- A new family of nucleophiles for photoinduced, copper-catalyzed cross-couplings via single-electron transfer: Reactions of thiols with aryl halides under mild conditions (O C)
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Building on the known photophysical properties of well-defined copper-carbazolide complexes, we have recently described photoinduced, copper-catalyzed N-arylations and N-alkylations of carbazoles. Until now, there have been no examples of the use of other families of heteroatom nucleophiles in such photoinduced processes. Herein, we report a versatile photoinduced, copper-catalyzed method for coupling aryl thiols with aryl halides, wherein a single set of reaction conditions, using inexpensive CuI as a precatalyst without the need for an added ligand, is effective for a wide range of coupling partners. As far as we are aware, copper-catalyzed C-S cross-couplings at 0 C have not previously been achieved, which renders our observation of efficient reaction of an unactivated aryl iodide at -40 C especially striking. Mechanistic investigations are consistent with these photoinduced C-S cross-couplings following a SET/radical pathway for C-X bond cleavage (via a Cu(I)-thiolate), which contrasts with nonphotoinduced, copper-catalyzed processes wherein a concerted mechanism is believed to occur.
- Uyeda, Christopher,Tan, Yichen,Fu, Gregory C.,Peters, Jonas C.
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supporting information
p. 9548 - 9552
(2013/07/19)
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- Chan-lam-type s-arylation of thiols with boronic acids at room temperature
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In this work, an efficient CuSO4-catalyzed S-arylation of thiols with aryl and heteroaryl boronic acids at room temperature is established. This catalytic system can tolerate a wide variety of thiols and arylboronic acids in the presence of only 5 mol % of CuSO4 as the catalyst and inexpensive 1,10-phen?H2O as the ligand. Moreover, this catalytic system used environment-friendly solvent (EtOH) and oxidant (oxygen).
- Xu, Hua-Jian,Zhao, Yong-Qiang,Feng, Teng,Feng, Yi-Si
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experimental part
p. 2878 - 2884
(2012/05/04)
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- Efficient copper(I)-catalyzed C-S cross-coupling of thiols with aryl halides in an aqueous two-phase system
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A mild and convenient C-S bond formation reaction catalyzed by CuI/L-proline in an aqueous two-phase system was achieved, providing a simple method for the synthesis of aryl sulfides in good yields.
- Zhang, Xin-Yan,Zhang, Xiao-Yan,Guo, Sheng-Rong
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experimental part
p. 23 - 35
(2011/12/05)
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- Zinc-mediated palladium-catalyzed formation of carbon-sulfur bonds
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(Chemical Equation Presented) A catalytic amount of zinc chloride in combination with a palladium catalyst ligated by a monodentate phosphine allows the coupling of aryl and alkyl thiols with aryl bromides in high yields. The addition of zinc chloride to a palladium catalyst system that reportedly failed to promote sulfide formation allows this once ineffective catalyst system to provide the sulfide product in good yield. This paper describes a high-yielding and general monodentate phosphine-ligated palladium catalyst for biaryl and alkyl aryl sulfide formation.
- Eichman, Chad C.,Stambuli, James P.
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supporting information; experimental part
p. 4005 - 4008
(2009/10/02)
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- Application of Regioselective Thiophene Lithiation to the Synthesis of Thiophene Analogues of Xanthones and Thioxanthones
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Treatment of 3-(p-tolyloxy)thiophene (3) with phenyllithium followed by carbonation with CO2 was found to be a convenient procedure for the preparation of the thiophene-2-carboxylic acid 4, which was cyclized to 5 with PPE.Treatment of 3 with butyllithium followed by carbonation gave the thiophene-2,5-dicarboxylic acid 8 which was cyclized to 9.Alkaline permanganate oxidation of 4 gave the diacid 10, which was cyclized to the tricyclic acid 11.Similar lithiation reactions were observed with additional 3-(aryloxy)thiophenes and with 3-(arylthio)thiophenes, and xanthone analogues were prepared from the resulting intermediates.
- Watthey, Jeffrey W.,Desai, Mahesh
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p. 1755 - 1759
(2007/10/02)
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