- Convenient MW-assisted synthesis of unsymmetrical sulfides using sulfonyl hydrazides as aryl thiol surrogate
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An efficient synthesis of unsymmetrical sulfides has been achieved via the cross-coupling reaction of aryl/het-aryl/benzyl halides with stable and easily workable sulfonyl hydrazides as thiol substitutes by means of [DBU][HOAc] and CuI under microwave irr
- Singh, Neetu,Singh, Rahul,Raghuvanshi, Dushyant S.,Singh, Krishna Nand
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Read Online
- Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides
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A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalcogenides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalcogenides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV-Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.
- Pan, Lei,Cooke, Maria Victoria,Spencer, Amara,Laulhé, Sébastien
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p. 420 - 425
(2021/11/01)
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- Thiolate-assisted copper(i) catalyzed C-S cross coupling of thiols with aryl iodides: scope, kinetics and mechanism
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Transition metal catalyzed coupling of thiols with aryl iodide offers a convenient method for accessing C-S linkage in organic synthesis. Herein, we report an efficient and practical method for the C-S cross coupling of thiophenols with aryl iodides using a Cu(i) catalyst. A diverse set of thiophenols is coupled with electron rich and poor aryl iodides to obtain diaryl sulfides in good to excellent yields. Noteworthily, these reactions proceed smoothly in polar protic solvents and under ligand-free environments. This procedure also finds application in the synthesis of 2-aminophenyl sulfide derivatives via ring opening of readily available benzothiazole. Furthermore, we performed kinetics and computational studies to understand the mechanism of the Cu(i) catalyzed reaction in the absence of a ligand. Hammett plots of the reaction rates versus the substituent constant show that these coupling reactions are modestly sensitive to the substituents on thiophenols as well as aryl iodides, indicating the involvement of both the reactants in the rate-determining step of the reaction. On the other hand, computational investigations of the different mechanistic pathways suggest that the strong coordination of thiolate to Cu may generate the catalytically competent intermediate [Cu(SPh)2]K which can initiate the catalytic cycle. The pathway initiated by [Cu(SPh)2]K is predicted to proceed through the lowest energy transition states and intermediates relative to the separated reactants.
- Bakare, Sneha Prasad,Patil, Mahendra
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p. 6283 - 6295
(2022/03/31)
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- 2-Pyridyl Sulfoxide Directed Pd(II)-Catalyzed C-H Olefination of Arenes with Molecular Oxygen as the Sole Oxidant
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Pd(II)-catalyzed C-H olefination of aryl 2-pyridyl sulfoxides with unactivated and activated olefins has been demonstrated. We employed environmentally benign and inexpensive molecular oxygen as the sole oxidant. The versatile nature of the 2-pyridyl sulf
- Yadav, Mamta,Jat, Ram Singh,Sarma, Bibek,Bhanuchandra
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p. 2269 - 2276
(2021/03/03)
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- Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
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We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.
- Zhao, Bin,Hammond, Gerald B.,Xu, Bo
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supporting information
(2021/09/13)
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- Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides
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Redox-active benzimidazolium sulfonamides as thiolating reagents have been developed for reductive C-S bond coupling. The IMDN-SO2R reagent provides a bench-stable cationic precursor to generate a portfolio of highly active N-S intermediates, which can be successfully applied in cross-electrophilic coupling with various organic halides. The employment of an electrophilic sulfur source solved the problem of catalyst deactivation and avoided odorous thiols, featuring practical conditions, broad substrate scope, and excellent tolerance.
- Zhang, Weigang,Huang, Mengjun,Zou, Zhenlei,Wu, Zhengguang,Ni, Shengyang,Kong, Lingyu,Zheng, Youxuan,Wang, Yi,Pan, Yi
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p. 2509 - 2514
(2021/03/01)
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- Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines
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An S-selective arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. This modular methodology permits selective introduction of functional groups from commercially available pyridyl halides, furnishing symmetrical and unsymmetrical 2,2′- A nd 2,3′-bipyridines. Iterative application of the methodology enabled the synthesis of a functionalized terpyridine with three different pyridine components.
- Duong, Vincent K.,Horan, Alexandra M.,McGarrigle, Eoghan M.
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supporting information
p. 8451 - 8457
(2020/11/12)
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- Direct C-S bond formation: Via C-O bond activation of phenols in a crossover Pd/Cu dual-metal catalysis system
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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
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p. 4491 - 4497
(2019/05/17)
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- 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
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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
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- Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and NH-sulfoximines
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We provide efficient synthetic access to heteroaryl sulfones in two-steps using a simple palladium–1,1′-bis[(diphenyl)phosphanyl]ferrocene catalyst to form in high yields variously functionalized heteroaromatic thioethers. Pyridinyl-containing substrates can be subsequently selectively oxidized into sulfones and NH-sulfoximines by using very mild oxidation conditions with a high functional group tolerance. In the palladium-catalyzed C–S coupling of heteroaromatic thiols, reactivity limitation is attached with electron-deficient thiols. We show that this limitation can be resolved by the successful use of 2-bromoheteroarenes in the C–S coupling. We established herein that this choice of heteroaryl electrophilic reagent in palladium-catalyzed C–S bond formation allows overcoming palladium dithiolate out-of-cycle resting state inertness. This was illustrated in the stoichiometric reactivity study of the palladium dithiolate formed from 4-trifluoromethylbenzen-1-thiol –isolated and characterized by multinuclear NMR and XRD– with both 2-chloropyridine and 2-bromopyridine.
- Guilbaud, Johan,Labonde, Marine,Selmi, Awatef,Kammoun, Majed,Cattey, Hélène,Pirio, Nadine,Roger, Julien,Hierso, Jean-Cyrille
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- Nickel(II) N-Heterocyclic Carbene Complexes: Versatile Catalysts for C–C, C–S and C–N Coupling Reactions
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A variety of NiII complexes with a wide range of electronic and steric properties, bearing picolylimidazolidene ligands (a–g) and Cp (Cp = η5-C5H5; 2a–f) or Cp* (Cp* = η5-C5Me5; 3a, c, g) groups, have been synthesised and characterised by using NMR spectroscopy and single-crystal X-ray crystallography. The complexes have been used as precatalysts for a wide range of catalytic transformations, which most likely involve a Ni0/NiII catalytic cycle. In particular, the new well-defined 2a, 2c, 3a and 3c complexes have demonstrated great efficiency and versatility towards Suzuki–Miyaura coupling reactions, hydroamination of activated olefins and C–S cross-coupling reactions of aryl halides and thiols under mild conditions.
- Junquera, Lourdes Benítez,Fernández, Francys E.,Puerta, M. Carmen,Valerga, Pedro
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supporting information
p. 2547 - 2556
(2017/05/29)
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- Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source
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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
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p. 5025 - 5038
(2017/10/06)
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- Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction
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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
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p. 5580 - 5585
(2016/10/21)
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- Nature of the copper-oxide-mediated C-S cross-coupling reaction: Leaching of catalytically active species from the metal oxide surface
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Copper-oxide-catalyzed cross-coupling reaction is a well-known strategy in heterogeneous catalysis. A large number of applications have been developed, and catalytic cycles have been proposed based on the involvement of the copper oxide surface. In the present work, we have demonstrated that copper(I) and copper(II) oxides served as precursors in the coupling reaction between thiols and aryl halides, while catalytically active species were formed upon unusual leaching from the oxide surface. A powerful cryo-SEM technique has been utilized to characterize the solution-state catalytic system by electron microscopy. A series of different experimental methods were used to reveal the key role of copper thiolate intermediates in the studied catalytic reaction. The present study shows an example of leaching from a metal oxide surface, where the leaching process involved the formation of a metal thiolate and the release of water. A new synthetic approach was developed, and many functionalized sulfides were synthesized with yields of up to 96%, using the copper thiolate catalyst. The study suggests that metal oxides may not act as an innocent material under reaction conditions; rather, they may represent a source of reactive species for solution-state homogeneous catalysis.
- Panova, Yulia S.,Kashin, Alexey S.,Vorobev, Maxim G.,Degtyareva, Evgeniya S.,Ananikov, Valentine P.
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p. 3637 - 3643
(2016/07/06)
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- 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
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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.
- Movassagh, Barahman,Takallou, Ahmad,Mobaraki, Akbar
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- (1H-benzo[d][1,2,3]triazol-1-yl)methanol: An efficient bidentate ligand for copper catalyzed S-arylation of thiols
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An operationally simple, palladium-free synthetic protocol for thio-arylation using 0.5 mol % CuI and 1 mol % (1H-benzo[d][1,2,3]triazol-1-yl)methanol as ligand is described. The ligand was found to be cheap, thermally stable, easy to synthesize, show simplicity in use and wide use in coupling reactions. Appropriately, the donor ability of the N=N bond of the benzotriazole ring and lone pair of electrons on the hydroxy group increases the bidentate ability of the ligand. Using this protocol, we have shown that a variety of aryl sulfides that can be synthesized in excellent yields from readily available aryl halide and thiols.
- Jhaa, Rajeev Ranjan,Choudharya, Deepak,Verma, Akhilesh K.
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p. 451 - 458
(2019/01/21)
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- Nickel-catalyzed C-S bond formation: Synthesis of aryl sulfides from arylsulfonyl hydrazides and boronic acids
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A practical nickel-catalysed approach has been developed for the C-S bond formation through the cross-coupling of arylsulfonyl hydrazides and aryl boronic acids. The report employs arylsulfonyl hydrazide as an aryl thiol equivalent and offers a mild and eco-safe synthesis of unsymmetrical thioethers in good to excellent yields in air. The scope and versatility of the method has been successfully demonstrated with 22 examples.
- Singh, Rahul,Allam, Bharat Kumar,Singh, Neetu,Kumari, Kumkum,Singh, Satish Kumar,Singh, Krishna Nand
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supporting information
p. 1181 - 1186
(2015/04/22)
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- Palladium Nanoparticles Immobilized on Nanosilica Triazine Dendritic Polymer (Pd np -nSTDP) as Catalyst in the Synthesis of Mono-, Di-, and Trisulfides through C-S Cross-Coupling Reactions
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A wide variety of diaryl sulfides has been synthesized in excellent yields via C-S cross-couplings of aryl/heteroaryl halides with aromatic/heteroaromatic thiols in the presence of palladium nanoparticles immobilized on nanosilica triazine dendritic polymer (Pd np -nSTDP) as a reusable catalyst under thermal conditions and microwave irradiation. Pd np -nSTDP also showed excellent catalytic activity for the preparation of a series of di- and trisulfides with benzene, pyridine, pyrimidine, and/or 1,3,5-triazine as the central cores by one-pot multi C-S cross-coupling reactions. Georg Thieme Verlag Stuttgart. New York.
- Isfahani, Amir Landarani,Mohammadpoor-Baltork, Iraj,Mirkhani, Valiollah,Moghadam, Majid,Khosropour, Ahmad Reza,Tangestaninejad, Shahram,Nasr-Esfahani, Mahboobeh,Rudbari, Hadi Amiri
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supporting information
p. 645 - 652
(2014/04/03)
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- Synthesis of heteroaryl containing sulfides via enaminone ligand assisted, copper-catalyzed C-S coupling reactions of heteroaryl thiols and aryl halides
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The C-S cross coupling reactions between electron deficient heteroaryl thiols and aryl halides have been smoothly performed to provide various heteroaryl containing sulfides in the presence of copper catalyst and enaminone ligand. the Partner Organisations 2014.
- Liu, Yunyun,Huang, Bin,Cao, Xiaoji,Wu, Dan,Wan, Jie-Ping
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p. 37733 - 37737
(2014/11/07)
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- Sulfur-silicon bond activation catalysed by Cl/Br ions: Waste-free synthesis of unsymmetrical thioethers by replacing fluoride catalysis and fluorinated substrates in SNAr reactions
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In contrast to conventional activation of Nu-SiR3 reagents by F ion attributed to the strong affinity of Si to F, S-Si activation can now be achieved using Cl/Br ions of TBAX as catalysts via formation of weaker X-Si bonds and Me3Si-X. This led to a waste-free synthesis of unsymmetrical thioethers via F-free SNAr reactions of activated (hetero)aryl halides and RS-SiMe3, with recovery of the useful Me3Si-X reagent in high yields. This journal is the Partner Organisations 2014.
- Jia, Xiaojuan,Yu, Lei,Liu, Jianping,Xu, Qing,Sickert, Marcel,Chen, Lianhui,Lautens, Mark
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supporting information
p. 3444 - 3449
(2014/07/08)
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- Thioetherification of Chloroheteroarenes: A Binuclear Catalyst Promotes Wide Scope and High Functional-Group Tolerance
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A constrained binuclear palladium catalyst system affords selective thioetherification of a wide range of functionalized arenethiols with chloroheteroaromatic partners with the highest turnover numbers (TONs) reported to date and tolerates a large variety of reactive functions. The scope of this system includes the coupling of thiophenols with six- and five-membered 2-chloroheteroarenes (i.e., functionalized pyridine, pyrazine, quinoline, pyrimidine, furane, and thiazole) and 3-bromoheteroarenes (i.e., pyridine and furane). Electron-rich congested thiophenols and fluorinated thiophenols are also suitable partners. The coupling of unprotected amino-2-chloropyridines with thiophenol and the successful employment of synthetically valuable chlorothiophenols are described with the same catalyst system. DFT studies attribute the high performance of this binuclear palladium catalyst to the decreased stability of thiolate-containing resting states. Palladium loading was as low as 0.2 mol %, which is important for industrial application and is a step forward in solving catalyst activation/deactivation problems.
- Platon, Mélanie,Wijaya, Novi,Rampazzi, Vincent,Cui, Luchao,Rousselin, Yoann,Saeys, Mark,Hierso, Jean-Cyrille
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p. 12584 - 12594
(2016/08/25)
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- KF/clinoptilolite: An efficient promoter for the synthesis of thioethers
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Potassium fluoride impregnated on natural zeolite as a new solid base system effectively catalyzes the coupling of thiophenols with electron-deficient fluoro-, chloro- and bromo-arenes in DMSO. This versatile and efficient solid base has been demonstrated to afford the corresponding desired products in good to excellent yields. This procedure provides a convenient, efficient and practical method for the preparation of diaryl thioethers.
- Salmanpour, Sadegh,Khalilzadeh, Mohammad A.,Hosseini, Abolfazl
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p. 339 - 344
(2013/07/28)
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- 2-(1-benzotriazolyl)pyridine: A robust bidentate ligand for the palladium-catalyzed C-C (Suzuki, Heck, Fujiwara-Moritani, Sonogashira), C-N and C-S coupling reactions
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A new class of bidentate ligand, 1-(pyridine-2-yl)-1H-benzo[d][1,2,3] triazole has been designed and employed for the palladium-catalyzed C-C (Suzuki, Heck, Fujiwara-Moritani, and Sonogashira), C-N and C-S coupling reactions. The ligand was found to be inexpensive, thermally stable, easy to synthesize from easily accessible starting materials on a multigram scale, show simplicity in use, and robustness in application, making this ligand effective for different coupling reactions. Suitably, the donor ability of the N=N bond of the benzotriazole ring and lone pair of electrons on the N of the pyridine ring enhance the bidentate ability of the ligand.
- Verma, Akhilesh K.,Jha, Rajeev R.,Chaudhary, Ritu,Tiwari, Rakesh K.,Danodia, Abhinandan K.
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p. 421 - 438
(2013/05/08)
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- Palladium-catalyzed regioselective arylation of arene C-H bond assisted by the removable 2-pyridylsulfinyl group
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A palladium-catalyzed arylation of arene C-H bond assisted by a removable 2-pyridylsulfinyl group is described. The reaction employs aryltrifluoroborates as the arylation reagent, leading to the corresponding products in moderate to good yield with broad substrate scope. The directing group can be removed or converted to other useful functionalities, which showcases the potential synthetic application of the methodology. Georg Thieme Verlag Stuttgart · New York.
- Zhang, Xunbin,Yu, Ming,Yao, Jinzhong,Zhang, Yuhong
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supporting information; experimental part
p. 463 - 467
(2012/03/11)
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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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- 2-pyridyl sulfoxide: A versatile and removable directing group for the PdII-catalyzed direct C-H olefination of arenes
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Removable and versatile: The 2-pyridylsulfinyl group has proved to be an efficient directing group in the PdII-catalyzed aryl ortho C-H olefination. This catalyst system enables the sequential double olefination to give asymmetrically di-ortho-functionalized arenes. The sulfinyl directing group can be easily cleaved, providing access to 1,3-disubstituted arenes, or transformed into a thiol group.
- Garcia-Rubia, Alfonso,Fernandez-Ibanez, M. Ungeles,Gomez Arrayas, Ramon,Carretero, Juan Carlos
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supporting information; experimental part
p. 3567 - 3570
(2011/05/12)
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- Palladium(II)-catalyzed direct alkenylation and arylation of arenes: Removable 2-pyridylsulfinyl group assisted C-H bond activation
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Palladium-catalyzed C-H activation reactions directed by a removable 2-pyridylsulfinyl group were developed. Aromatic olefination products were formed in good yields on treatment of 2-(phenylsulfinyl)pyridines with alkenes in the presence of a Pd catalyst
- Yu, Ming,Liang, Zunjun,Wang, Yongyong,Zhang, Yuhong
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experimental part
p. 4987 - 4994
(2011/08/03)
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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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- Catalyst-free and base-free water-promoted SNAr reaction of heteroaryl halides with thiols
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A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products. Georg Thieme Verlag Stuttgart.
- Sreedhar,Surendra Reddy,Amarnath Reddy
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experimental part
p. 1732 - 1738
(2009/12/26)
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- A general and efficient CuI/BtH catalyzed coupling of aryl halides with thiols
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We report an exceptionally mild, general and efficient copper catalyzed cross coupling reaction of aryl bromides and thiols using 0.5 mol % CuI and 1 mol % benzotriazole. Experimental simplicity, generality, functional group tolerance and low cost of the catalyst are advantages of the protocol.
- Verma, Akhilesh Kumar,Singh, Jaspal,Chaudhary, Ritu
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p. 7199 - 7202
(2008/03/11)
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- Green chemical synthesis of 2-benzenesulfonyl-pyridine and related derivatives
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A practical synthesis of 2-benzenesulfonylpyridine, 1, is described which is a key starting material for the manufacture of an investigational new drug candidate at Eli Lilly and Company. An optimized green chemical process was developed which features a novel tandem SNAr/oxidation under mild conditions to produce the target sulfone, 1, in 86% yield and>99% purity. In addition, this novel, environmentally friendly methodology was found to be general for the synthesis of substituted aromatic pyridyl sulfides and sulfones.
- Trankle, William G.,Kopach, Michael E.
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supporting information
p. 913 - 917
(2012/12/30)
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- THE REACTION OF 2,2'-DIPYRIDYL SULFIDE WITH PHENOL
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The reaction of 2,2'-dipyridyl sulfide with phenol affords 2-pyridinethiol and phenyl 2-pyridyl ether, which is the aromatic ipso substitution in 2,2'-dipyridyl sulfide by the phenoxy group.On the other hand, pyridyl tolyl sulfide is formed by the reaction of phenyl pyridyl ether with toluenethiol.
- Inoue, Shordoh
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p. 141 - 144
(2007/10/02)
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