- A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst
-
Covalent Organic Frameworks (COFs) have recently emerged as light-harvesting devices, as well as elegant heterogeneous catalysts. The combination of these two properties into a dual catalyst has not yet been explored. We report a new photosensitive triazine-based COF, decorated with single Ni sites to form a dual catalyst. This crystalline and highly porous catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur–carbon cross-coupling reaction. Incorporation of single transition metal sites in a photosensitive COF scaffold with two-component synergistic catalyst in organic transformation is demonstrated for the first time.
- Chen, Hui,Liu, Wanlu,Laemont, Andreas,Krishnaraj, Chidharth,Feng, Xiao,Rohman, Fadli,Meledina, Maria,Zhang, Qiqi,Van Deun, Rik,Leus, Karen,Van Der Voort, Pascal
-
-
Read Online
- Synthesis of diaryl sulfides via nickel ferrite-catalysed C─S bond formation in green media
-
NiFe2O4 magnetic nanoparticles (MNPs) were synthesized, characterized and applied as an air-stable, inexpensive and magnetically separable nanocatalyst for the synthesis of structurally diverse sulfides. Efficient methodologies were developed for the synthesis of unsymmetric diaryl sulfides via odourless and one-pot reactions of triphenyltin chloride/S8 or arylboronic acid/S8 as thiolating agents with aryl halides or nitroarenes as starting materials in the presence of base (K2CO3 or NaOH) and NiFe2O4 MNPs as a catalyst in water or poly (ethylene glycol) as solvent at 80–110?°C. Free from ligand and the unpleasant smell of thiols and with the use of magnetically reusable nanocatalyst, green solvents and commercially available and cheap sulfur source and starting materials, these methods are more eco-friendly and practical than available protocols for the synthesis of sulfides.
- Farzin, Shiva,Rahimi, Abdollah,Amiri, Kamran,Rostami, Abed,Rostami, Amin
-
-
Read Online
- Ligand-free Cu-catalyzed odorless synthesis of unsymmetrical sulfides through cross-coupling reaction of aryl/benzyl/alkyl halides with an aryl boronic acid/S8 system as a thiolating agent in PEG
-
In this article, we have presented a novel, efficient and environmentally benign method for one-pot, one-step and odorless synthesis of a wide range of unsymmetrical sulfides from the reaction of aryl/benzyl/alkyl halides with aryl boronic acids in the presence of S8, NaOH and a catalytic amount of CuI in PEG200 as green solvent at 40-60 °C. The products were obtained in moderate to excellent yields. More importantly, this reaction is applicable for the gram-scale preparation of the desired sulfides.
- Rostami, Amin,Rostami, Abed,Ghaderi, Arash,Zolfigol, Mohammad Ali
-
-
Read Online
- Direct C-S bond formation: Via C-O bond activation of phenols in a crossover Pd/Cu dual-metal catalysis system
-
A dual-metal catalysis system including a newly prepared nanoparticle [SiO2@organic-linker(OL)@Pd(II)] and CuI was introduced with ultra-high catalytic activity (high turnover number (TON), up to 19000) to a one-pot and odorless synthesis of unsymmetrical aryl sulfides by crossover C-S bond formation. The reaction proceeds via C-O bond activation of phenols and direct C-S bond formation in the presence of S8 as an oddorless sulfur source and aryl boronic acids under mild conditions (room temperature). The catalyst could be recycled up to five times without an obvious change in its activity.
- Khakyzadeh, Vahid,Rostami, Abed,Veisi, Hojat,Shirmardi Shaghasemi, Behzad,Reimhult, Erik,Luque, Rafael,Xia, Yuanzhi,Darvishi, Sima
-
-
Read Online
- NiFe2O4 as a magnetically recoverable nanocatalyst for odourless C–S bond formation via the cleavage of C–O bond in the presence of S8 under mild and green conditions
-
We present green methodologies for one-pot and odourless syntheses of unsymmetric and symmetric diaryl sulfides via C─O bond activation using NiFe2O4 magnetic nanoparticles as a reusable heterogeneous nanocatalyst. The synthesis of unsymmetric sulfides is performed using the cross-coupling reaction of phenolic esters such as acetates, triflates and tosylates with arylboronic acid/S8 or triphenyltin chloride/S8 as thiolating agents in the presence of base and NiFe2O4 magnetic nanoparticles as a catalyst in poly(ethylene glycol) as solvent at 60–85°C. Also, the synthesis of symmetric diaryl sulfides from phenolic compounds using S8 as the sulfur source and NiFe2O4 as catalyst in dimethylformamide at 120°C is described. Using these protocols, the syntheses of various unsymmetric and symmetric sulfides become easier than using the available protocols due to the use of a magnetically reusable bimetallic nanocatalyst and avoiding the use of thiols and aryl halides.
- Atashkar, Bahareh,Rostami, Amin,Rostami, Abed,Zolfigol, Mohammad Ali
-
-
Read Online
- Silver catalyzed C-C and C-S coupling of aryl halides and thiols with boronic acids
-
An efficient Ag(I) catalyzed carbon-carbon and carbon-sulfur bond formation reaction of aryl halides and thiols with boronic acids has been demonstrated. Using this protocol, substrates with a wide range of functional group including electron-rich, and electron deficient substituents have been explored. These reactions are particularly useful to prepare symmetrical and unsymmetrical biphenyls and thioethers. These products were isolated in high yield.
- Das, Rima,Chakraborty, Debashis
-
-
Read Online
- Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source
-
Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.
- Rostami, Abed,Rostami, Amin,Ghaderi, Arash,Gholinejad, Mohammad,Gheisarzadeh, Sajedeh
-
-
Read Online
- Synthesis of diaryl sulfides based on copper-doped OMS-2
-
We describe a practical protocol for efficiently preparing diaryl sulfide compounds using Cu–OMS-2 as the catalyst. Cu–OMS-2 originates from manganese oxide octahedral molecular sieves modified with copper ions and catalyzes the C–S coupling reaction of substituted thiophenols and aryl halides. This protocol has the advantages of environmental friendliness, simple operation, high yields, good tolerance of functional groups, and the Cu–OMS-2 catalytic material can be recycled several times.
- Yu, Shao-Qiang,Liu, Na,Liu, Ming-Guo,Wang, Long
-
p. 237 - 241
(2020/11/30)
-
- Coupling of thiols and aromatic halides promoted by diboron derived super electron donors
-
We have proven that pyridine-boryl complexes can be used as superelectron donors to promote the coupling of thiols and aromatic halides through a SRN1 mechanism. The reaction is efficient for a broad substrate scope, tolerating heterocycles including pyridines, enolizable or reducible functional groups. The method has been applied to intermediates in drug synthesis as well as interesting functionalized polythioethers through a controlled and consecutive intramolecular electron transfer process.
- Franco, Mario,Vargas, Emily L.,Tortosa, Mariola,Cid
-
supporting information
p. 11653 - 11656
(2021/11/12)
-
- Paired Electrolysis Enabled Ni-Catalyzed Unconventional Cascade Reductive Thiolation Using Sulfinates
-
Herein, we have reported a nickel-catalyzed cascade reductive thiolation of aryl halides with sulfinates driven by paired electrolysis. This protocol uses sulfinates as the sulfur source, and various thioethers could be synthesized under mild conditions. By mechanism exploration, we find that a cascade chemical step is allowed on the electrode interface and could alter the reaction pathway in paired electrolysis, whose findings could help the discovery of novel cascade reactions with unique reactivity.
- Kang, Jun-Chen,Li, Zi-Hao,Chen, Chao,Dong, Li-Kun,Zhang, Shu-Yu
-
supporting information
p. 15326 - 15334
(2021/10/25)
-
- Nickel-Catalyzed Decarbonylative Thioetherification of Acyl Fluorides via C-F Bond Activation
-
Nickel-catalyzed decarbonylative thioetherification of acyl fluorides has been developed. This transformation allows an array of acyl fluorides to react with thiophenols. A wide range of functional groups are well tolerated and the corresponding sulfides can be obtained in good to excellent yields. This protocol provides the formation of diverse carbon-sulfur bonds via a highly efficient decarbonylative process.
- You, Jingwen,Chen, Qiang,Nishihara, Yasushi
-
supporting information
p. 3045 - 3050
(2021/05/31)
-
- Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2
-
An efficient electrochemical synthesis approach of various unsymmetrical thioethers and arylboronates has been developed. Bench stable arylazo sulfones were used as radical precursors for carbon-heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and even added bases, but also exhibited favorable functional group tolerance. (Figure presented.).
- Wang, Rongkang,Chen, Fangming,Jiang, Lvqi,Yi, Wenbin
-
supporting information
p. 1904 - 1911
(2021/02/12)
-
- Method for synthesizing diarylthioether compound by using manganese oxide molecular sieve doped copper catalyst
-
The invention relates to a synthesis method of a diarylthioether compound by catalyzing with heterogeneous manganese oxide octahedral molecular sieve doped copper (Cu-OMS-2). The chemical structural formula of the compound is shown in the description, whe
- -
-
Paragraph 0020-0022
(2020/12/08)
-
- Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
-
An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.
- Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
-
p. 2707 - 2712
(2020/03/11)
-
- 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 template free protocol for fabrication of a Ni(ii)-loaded magnetically separable nanoreactor scaffold for confined synthesis of unsymmetrical diaryl sulfides in water
-
In the present report, an environmentally benign magnetically recoverable nickel(ii)-based nanoreactor as a heterogeneous catalyst has been developedviaa template free approach. The catalytic performance of the synthesized catalyst is assessed in the confined oxidative coupling of arenethiols with arylhydrazines to form unsymmetrical diaryl sulfides under aerobic conditions. The salient features of our protocol include oxidant- and ligand-free conditions, use of water as a green solvent, room temperature and formation of nitrogen and water as the only by-products. Moreover, a broad range of functional groups are tolerated well and provide the corresponding diaryl sulfides in moderate to good yields. Moreover, the heterogeneous nature of the catalyst permits facile magnetic recovery and reusability for up to seven runs, making the present protocol highly desirable from industrial and environmental standpoints.
- Arora, Gunjan,Gaur, Rashmi,Gupta, Radhika,Rana, Pooja,Sharma, Rakesh Kumar,Yadav, Manavi,Yadav, Priya
-
p. 19390 - 19396
(2020/06/04)
-
- C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
-
An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.
- Xuan, Maojie,Lu, Chunlei,Lin, Bo-Lin
-
supporting information
(2019/08/26)
-
- Electrochemically Promoted Nickel-Catalyzed Carbon-Sulfur Bond Formation
-
This work describes a nickel-catalyzed Ullmann-type thiolation of aryl iodidesunder mild electrochemical conditions. The simple undivided cell with graphene/nickel foam electrode setups offers excellent substrate tolerance, affording aryl and alkyl sulfides in good chemical yields. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated by cyclic voltammetry.
- Wang, Yang,Deng, Lingling,Wang, Xiaochen,Wu, Zhengguang,Wang, Yi,Pan, Yi
-
p. 1630 - 1634
(2019/03/08)
-
- Structure-Activity Relationship Studies of Tolfenpyrad Reveal Subnanomolar Inhibitors of Haemonchus contortus Development
-
Recently, we have discovered that the registered pesticide, tolfenpyrad, unexpectedly and potently inhibits the development of the L4 larval stage of the parasitic nematode Haemonchus contortus with an IC50 value of 0.03 μM while displaying good selectivity, with an IC50 of 37.9 μM for cytotoxicity. As a promising molecular template for medicinal chemistry optimization, we undertook anthelmintic structure-activity relationships for this chemical. Modifications of the left-hand side (LHS), right-hand side (RHS), and middle section of the scaffold were explored to produce a set of 57 analogues. Analogues 25, 29, and 33 were shown to be the most potent compounds of the series, with IC50 values at a subnanomolar level of potency against the chemotherapeutically relevant fourth larval (L4) stage of H. contortus. Selected compounds from the series also showed promising activity against a panel of other different parasitic nematodes, such as hookworms and whipworms.
- Le, Thuy G.,Kundu, Abhijit,Ghoshal, Atanu,Nguyen, Nghi H.,Preston, Sarah,Jiao, Yaqing,Ruan, Banfeng,Xue, Lian,Huang, Fei,Keiser, Jennifer,Hofmann, Andreas,Chang, Bill C. H.,Garcia-Bustos, Jose,Wells, Timothy N. C.,Palmer, Michael J.,Jabbar, Abdul,Gasser, Robin B.,Baell, Jonathan B.
-
p. 1036 - 1053
(2019/01/14)
-
- CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
-
In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
- Mohammadinezhad, Arezou,Akhlaghinia, Batool
-
p. 15525 - 15538
(2019/10/19)
-
- Nickel-Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry
-
Transition-metal-catalyzed coupling reactions are useful tools for synthesizing aryl sulfur compounds. However, conventional transition-metal-catalyzed thiolation of aryl bromides and chlorides typically requires the use of strong base under elevated reaction temperature. Herein, we report the first examples of nickel-catalyzed electrochemical thiolation of aryl bromides and chlorides in the absence of an external base at room temperature using undivided electrochemical cells.
- Liu, Dong,Ma, Hong-Xing,Fang, Ping,Mei, Tian-Sheng
-
supporting information
p. 5033 - 5037
(2019/03/13)
-
- A semiconducting supramolecular Co(ii)-metallohydrogel: an efficient catalyst for single-pot aryl-S bond formation at room temperature
-
A novel mechanically stable supramolecular Co(ii)-metallohydrogel has been synthesized. Cobalt(ii) nitrate hexahydrate and monoethanolamine, as a low molecular weight organic gelator, are used to get the gel. The mechanical stability of the supramolecular hydrogel was analyzed. The morphology of the supramolecular metallohydrogel was scrutinized. The semiconducting features of the metallohydrogel were studied. The conducting properties of the Co(ii)-metallohydrogel establish a Schottky barrier diode type nature. The catalytic nature of the Co(ii)-metallohydrogel based room temperature single pot aryl-S coupling reaction was explored. Most interestingly, the Co(ii)-metallohydrogel based catalytic aryl-S coupling reaction does not require any column-chromatographic purification protocol to get pure aryl-thioethers. Thus, through this work a semiconducting Schottky barrier diode application and catalytic role in the room temperature single pot aryl-S coupling reaction of a supramolecular Co(ii)-metallohydrogel have been explored.
- Dhibar, Subhendu,Dey, Amiya,Jana, Rajkumar,Chatterjee, Arpita,Das, Gourab Kanti,Ray, Partha Pratim,Dey, Biswajit
-
supporting information
p. 17388 - 17394
(2019/12/02)
-
- Merging Photoredox and Organometallic Catalysts in a Metal–Organic Framework Significantly Boosts Photocatalytic Activities
-
Metal–organic frameworks (MOFs) have been extensively used for single-site catalysis and light harvesting, but their application in multicomponent photocatalysis is unexplored. We report here the successful incorporation of an IrIII photoredox catalyst and a NiII cross-coupling catalyst into a stable Zr12 MOF, Zr12-Ir-Ni, to efficiently catalyze C?S bond formation between various aryl iodides and thiols. The proximity of the IrIII and NiII catalytic components to each other (ca. 0.6 nm) in Zr12-Ir-Ni greatly facilitates electron and thiol radical transfers from Ir to Ni centers to reach a turnover number of 38 500, an order of magnitude higher than that of its homogeneous counterpart. This work highlights the opportunity in merging photoredox and organometallic catalysts in MOFs to effect challenging organic transformations.
- Zhu, Yuan-Yuan,Lan, Guangxu,Fan, Yingjie,Veroneau, Samuel S.,Song, Yang,Micheroni, Daniel,Lin, Wenbin
-
supporting information
p. 14090 - 14094
(2018/10/15)
-
- PHOTOCATALYST-FREE, LIGHT-INDUCED CARBON-SULFUR CROSS-COUPLING METHODS
-
In one aspect, the invention provides a method of promoting a carbon-sulfur bond forming reaction. In certain embodiments, the reaction comprises cross-coupling of a(n) (hetero)aryl halide with a thiol to form the carbon-sulfur bond, wherein the method is promoted by light irradiation in the absence of a photocatalyst. In other embodiments, the cross-coupling reaction can be promoted through visible light irradiation, including sunlight.
- -
-
Paragraph 0099; 0155; 0156
(2019/01/10)
-
- Visible-Light-Mediated Synthesis of Unsymmetrical Diaryl Sulfides via Oxidative Coupling of Arylhydrazine with Thiol
-
A metal-free visible-light-promoted oxidative coupling between thiols and arylhydrazines has been developed to afford diaryl sulfides using a catalytic amount of rose bengal as photocatalyst under aerobic conditions. A library of unsymmetrical diaryl sulfides with broad functionalities was synthesized in good yields at room temperature. The present methodology is also applicable to benzo[d]thiazole-2-thiols, benzo[d]oxazole-2-thiol, 1H-benzo[d]imidazole-2-thiols, and 1H-imidazole-2-thiol.
- Kibriya, Golam,Mondal, Susmita,Hajra, Alakananda
-
supporting information
p. 7740 - 7743
(2018/12/14)
-
- Visible-light-promoted C-S cross-coupling via intermolecular charge transfer
-
Disclosed is a mild, scalable, visible-lightpromoted cross-coupling reaction between thiols and aryl halides for the construction of C-S bonds in the absence of both transition metal and photoredox catalysts. The scope of aryl halides and thiol partners includes over 60 examples and therefore provides an entry point into various aryl thioether building blocks of pharmaceutical interest. Furthermore, to demonstrate its utility, this C-S coupling protocol was applied in drug synthesis and latestage modifications of active pharmaceutical ingredients. UV-vis spectroscopy and time-dependent density functional theory calculations suggest that visible-lightpromoted intermolecular charge transfer within the thiolate-aryl halide electron donor-acceptor complex permits the reactivity in the absence of catalyst.
- Liu, Bin,Lim, Chern-Hooi,Miyake, Garret M.
-
supporting information
p. 13616 - 13619
(2017/11/06)
-
- Rhodium-Catalyzed Synthesis of Unsymmetric Di(heteroaryl) Sulfides Using Heteroaryl Ethers and S-Heteroaryl Thioesters via Heteroarylthio Exchange
-
Unsymmetric di(heteroaryl) sulfides were synthesized by a rhodium-catalyzed heteroarylthio exchange reaction of heteroaryl aryl ethers and S-(heteroaryl) thioesters. The reaction has broad applicability, giving diverse unsymmetric di(heteroaryl) sulfides containing five- and six-membered heteroarenes. No base is required in this reaction, which has been developed by the judicious design of organic substrates.
- Arisawa, Mieko,Tazawa, Takeru,Tanii, Saori,Horiuchi, Kiyofumi,Yamaguchi, Masahiko
-
p. 804 - 810
(2017/04/26)
-
- An aryl thioether synthetic method of the compound
-
The invention discloses a synthetic method of an aryl sulfide type compound shown by a formula (3). In a reaction solvent, an aryl or alkenyl thiosulfate type derivative and a boric acid, boric acid grease or borate type derivative are used as reaction raw materials and react with each other to obtain a polysubstituted aryl sulfide type compound under the action of a metal copper catalyst. According to the synthetic method disclosed by the invention, reaction conditions are mild, raw materials are easily-available and low in price, the reaction operation is simple, the yield is relatively high, and a key skeleton structure is provided for the synthesis of many natural products and medicaments, so that the method can be widely applicable to industrial scale production. A formula is shown in the specification.
- -
-
Paragraph 0091; 0092; 0093; 0094
(2017/07/04)
-
- Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction
-
A facile aromatic nucleophilic substitution (SNAr) reaction in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments, 1H NMR and IR spectroscopies. This chemistry provides an efficient and metal-free approach for the generation of Caryl-X (XS, N, O) bonds, many of which are significant synthetic intermediates or drugs, making this methodology attractive to both synthetic and medicinal chemistry.
- Zhang, Xiao,Lu, Guo-Ping,Cai, Chun
-
p. 5580 - 5585
(2016/10/21)
-
- Tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex as an efficient and recyclable catalyst for coupling of aryl iodides with thiols
-
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.
- Yao, Fang,Zhang, Rongli,Wu, Yichao,Cai, Mingzhong
-
p. 612 - 616
(2015/11/27)
-
- A novel and efficient zinc-catalyzed thioetherification of aryl halides
-
The first zinc-catalysed protocol for the C-S cross-coupling reaction is reported. Zinc catalysis has an undeniable advantage over other catalytic systems as it is non-toxic, and the catalysts are easily available and cheap, with environmentally benign properties. This novel, efficient, palladium- and triphenylphosphine-free protocol yielded a variety of aryl and alkyl sulfides in moderate to excellent yields. This journal is
- Thankachan, Amrutha P.,Sindhu,Krishnan, K. Keerthi,Anilkumar, Gopinathan
-
p. 32675 - 32678
(2015/04/27)
-
- 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)
-
- CO2-promoted oxidative cross-coupling reaction for C-S bond formation via masked strategy in an odourless way
-
Cu-catalyzed direct oxidative cross-coupling between boronic acids and masked sulfides delivering thioethers was described, in which the SO3-, as a mask, has shown a distinctive effect on the oxidative cross-coupling condition. Disulfide could be suppressed efficiently via masked strategy under CO2 atmosphere. A broad scope of aromatics and scalable processes indicates its practicality, which could be further applied to drug late-stage modification and unsymmetrical dibenzothiophenes (DBTs) synthesis.
- Qiao, Zongjun,Ge, Nanyang,Jiang, Xuefeng
-
supporting information
p. 10295 - 10298
(2015/06/25)
-