10169-55-8Relevant articles and documents
Tilborg et al.
, p. 2113 (1977)
Palladium on charcoal as a recyclable catalyst for C - S cross-coupling of thiols with aryl halides under ligand-free conditions
Jiang, Zheng,She, Jin,Lin, Xufeng
, p. 2558 - 2562 (2009)
5-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides using a catalytic amount of palladium on charcoal as a heterogeneous catalysis with potassium hydroxide as the base in dimethyl sulfoxide (DMSO) at 110°C is accomplished in good yields. The C. - S bond formation reaction functions under ligand-free conditions, and the palladium on charcoal catalyst can be is reused for five runs without any loss of activity.
Cu2O/SiC as efficient catalyst for Ullmann coupling of phenols with aryl halides
Wang, Yibing,Guo, Xiaoning,Lü, Manqian,Zhai, Zhaoyang,Wang, Yingyong,Guo, Xiangyun
, p. 658 - 664 (2017)
A Cu2O/SiC heterogeneous catalyst was prepared via a two-step liquid-phase method using diethylene glycol as both the solvent and the reducing agent. The catalyst was characterized using X-ray diffraction, X-ray photoelectron spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and H2 temperature-programmed reduction. All the results indicate that Cu is present on the SiC support primarily as Cu2O. The SEM and TEM results show that cubic Cu2O nanoparticles are uniformly dispersed on the β-SiC surface. The reaction conditions, namely the temperature, reaction time, and amounts of base and catalyst used, for the Ullmann-type C–O cross-coupling reaction were optimized. A model reaction was performed using iodobenzene (14.0 mmol) and phenol (14.0 mmol) with Cu2O/SiC (5 wt% Cu) as the catalyst, Cs2CO3 (1.0 equiv.) as the base, and tetrahydrofuran as the solvent at 150 °C for 3 h; a yield of 97% was obtained and the turnover frequency (TOF) was 1136 h?1. The Cu2O/SiC catalyst has a broad substrate scope and can be used in Ullmann-type C–O cross-coupling reactions of aryl halides and phenols bearing a variety of different substituents. The catalyst also showed high activity in the Ullmann-type C–S cross-coupling of thiophenol with iodobenzene and substituted iodobenzenes; a TOF of 1186 h?1 was achieved. The recyclability of the Cu2O/SiC catalyst in the O-arylation of phenol with iodobenzene was investigated under the optimum conditions. The yield decreased from 97% to 64% after five cycles. The main reason for the decrease in the catalyst activity is loss of the active component, i.e., Cu2O.
The first N-heterocyclic carbene-based nickel catalyst for C-S coupling
Yugen, Zhang,Kao, Chin Ngeow,Ying, Jackie Y.
, p. 3495 - 3498 (2007)
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.
Magnetic nanoparticle-supported Pd(II)-cryptand 22 complex: An efficient and reusable heterogeneous precatalyst in the Suzuki-Miyaura coupling and the formation of aryl-sulfur bonds in honor and memory of late Prof. Mathias Mertes
Movassagh, Barahman,Takallou, Ahmad,Mobaraki, Akbar
, p. 55 - 65 (2015)
In the present work, silica-coated magnetic nanoparticles [Fe3O4@SiO2@C22-Pd(II)] were prepared and characterized by transmission electron microscopy, Fourier transform infrared spectroscopy, vibrating sample magnetometer, energy dispersive X-ray analysis, X-ray photoelectron spectroscopy, elemental analysis, inductively coupled plasma, thermogravimetric and differential thermal analysis. This heterogeneous catalyst is utilized as an effective catalyst for the Suzuki-Miyaura coupling of arylboronic acids and aryl halides, and the cross-coupling reaction of aryl halides and thiols. The catalyst was easily separated by magnetic decantation and the recovered catalyst was reused for five cycles without any significant loss of the catalytic activity.
Palladium-catalyzed C-S bond formation by using N-amido imidazolium salts as ligands
Byeun, Aleum,Baek, Kyungkyu,Han, Min Su,Lee, Sunwoo
, p. 6712 - 6715 (2013)
N-Amido imidazolium salt was employed as a ligand in the palladium-catalyzed cross-coupling reaction of aryl halides and thiols, and showed good activity in the formation of thioether. The best combination for the coupling with aryl bromides was N-amido imidazolium salt 2 and NaHMDS, and that for the coupling with aryl iodides was N-amido imidazolium salt 1 and KO tBu. The coupling reactions were conducted in the presence of Pd(OAc)2 (1 mol %) in DMSO at 80 C for 12 h.
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Tilborg,Smit
, p. 3651 (1977)
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Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols
Sperotto, Elena,Van Klink, Gerard P. M.,De Vries, Johannes G.,Van Koten, Gerard
, p. 5625 - 5628 (2008)
(Chemical Equation Presented) A protocol for the copper-catalyzed aryl-sulfur bond formation between aryl iodides and thiophenols is reported. The reaction is catalyzed by a low amount (1-2.5 mol %) of readily available and ligand-free copper iodide salt. A variety of diaryl thioethers are synthesized under relatively mild reaction conditions with good chemoselectivity and functional group tolerance.
The copper-nicotinamide complex: Sustainable applications in coupling and cycloaddition reactions
Baig, R.B. Nasir,Vaddula, Buchi Reddy,Nadagouda, Mallikarjuna N.,Varma, Rajender S.
, p. 1243 - 1248 (2015)
The crystalline copper(ii)-nicotinamide complex, synthesized via simple mixing of copper chloride and nicotinamide solution at room temperature, catalyzes the C-S, C-N bond forming and cycloaddition reactions under a variety of sustainable reaction conditions.
Efficient ligand-free copper-catalyzed C-S cross-coupling of thiols with aryl iodides using KF/Al2O3 as base
Feng, Yi-Si,Li, Yuan-Yuan,Tang, Lin,Wu, Wei,Xu, Hua-Jian
, p. 2489 - 2492 (2010)
We report a mild, convenient, environmentally friendly, and ligand-free synthetic protocol for the cross-coupling reaction of aryl iodides and thiols using 10 mol % CuI with KF/Al2O3 as the base, in DMF at 110 °C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available iodides and thiols.
Palladium-catalyzed Reaction of Stannyl Sulfide with Aryl Bromide. Preparation of Aryl Sulfide
Kosugi, Masanori,Ogata, Toshimi,Terada, Masahiro,Sano, Hiroshi,Migita, Toshihiko
, p. 3657 - 3658 (1985)
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Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals
Du, Ya,Pearson, Ryan M.,Lim, Chern-Hooi,Sartor, Steven M.,Ryan, Matthew D.,Yang, Haishen,Damrauer, Niels H.,Miyake, Garret M.
, p. 10962 - 10968 (2017)
Photoredox catalysis is a versatile approach for the construction of challenging covalent bonds under mild reaction conditions, commonly using photoredox catalysts (PCs) derived from precious metals. As such, there is need to develop organic analogues as sustainable replacements. Although several organic PCs have been introduced, there remains a lack of strongly reducing, visible-light organic PCs. Herein, we establish the critical photophysical and electrochemical characteristics of both a dihydrophenazine and a phenoxazine system that enables their success as strongly reducing, visible-light PCs for trifluoromethylation reactions and dual photoredox/nickel-catalyzed C?N and C?S cross-coupling reactions, both of which have been historically exclusive to precious metal PCs.
An efficient copper-catalyzed carbon-sulfur bond formation protocol in water
Ke, Fang,Qu, Yanyang,Jiang, Zhaoqiong,Li, Zhengkai,Wu, Di,Zhou, Xiangge
, p. 454 - 457 (2011)
An efficient protocol of copper-catalyzed C-S bond formation between aryl halides and potassium thiocyanate leading to diaryl sulfides is reported. A variety of diaryl sulfides can be synthesized in good to excellent yields up to 94%.
An efficient tris-(2-aminoethyl)amine-CuI-catalyzed thioetherification of thiols with aryl halides
Jogdand, Nivrutti R.,Shingate, Bapurao B.,Shingare, Murlidhar S.
, p. 6092 - 6094 (2009)
A robust method has been developed to couple a wide variety of thiols and aryl halides. The C-S bond forming reaction makes use of catalytic copper(I) iodide and the ligand tris-(2-aminoethyl)amine. These conditions tolerate a wide degree of functionality on both aryl halide and thiol reactants and have resulted in numerous examples being synthesized. Commercial availability of the ready to use, inexpensive ligand, tris-(2-aminoethyl)amine and air-stable CuI make the method well suited to generate a diverse array of diaryl thioethers.
Homoleptic and heteroleptic Zn(ii) selone catalysts for thioetherification of aryl halides without scrubbing oxygen
Vaddamanu, Moulali,Velappan, Kavitha,Prabusankar, Ganesan
, p. 3574 - 3583 (2020)
Five new mononuclear tetra-coordinated zinc(ii) selones, [Zn(L1)2Cl2] (1), [Zn(L1)2Br2] (2), [{Zn(L2)4}{BF4}2] (3), [{Zn(L2)4}{ClO4}2] (4), and [Zn(L2)2Br2] (5), have been isolated from a one-pot reaction between the corresponding zinc(ii) salt and selone ligand, 1-methyl 3-naphthylmethylimidazoline-2-selone (L1) or 1-isopropyl 3-methylimidazoline-2-selone (L2). All these complexes were characterized by CHN analysis, FT-IR, NMR studies, and single-crystal X-ray crystallography techniques. The Zn(ii) center in 1-5 exhibits a distorted tetrahedral geometry. Besides, 1-5 were employed as catalysts in the thioetherification of aryl halides. The first zinc(ii) catalyst-mediated thioetherification of aryl halides without scrubbing oxygen was demonstrated. Catalysts 1-5 are highly active towards the cross-coupling reaction between aryl halides and thiophenols. The catalytic ability of 1-5 was explored in THF, toluene, and CH3CN solvents with different bases such as K2CO3, Cs2CO3, and NaOtBu. Interestingly, the zinc(ii) center attached to two selone ligands is much more catalytically active than that attached to four selone ligands.
Tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex as an efficient and recyclable catalyst for coupling of aryl iodides with thiols
Yao, Fang,Zhang, Rongli,Wu, Yichao,Cai, Mingzhong
, p. 612 - 616 (2015)
The C-S coupling reaction of aryl iodides with thiols was achieved at 110 °C in DMF/dioxane (V/V, 1:9) in the presence of a tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex [MCM-41-3OH-CuI] with Cs2CO3 as base to afford a variety of diaryl sulfides in good to excellent yields. The MCM-41-3OH-CuI catalyst can be easily recovered by a simple filtration and reused for at least six times without significant loss of activity.
Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
, p. 8098 - 8103 (2021/10/25)
We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.
Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
, p. 10829 - 10837 (2021/07/28)
Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.
