- Environmentally Friendly and Recyclable CuCl 2-Mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent
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Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2-catalyzed C S bondformation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N'-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.
- Shen, Guodong,Lu, Qichao,Wang, Zeyou,Sun, Weiwei,Zhang, Yalin,Huang, Xianqiang,Sun, Manman,Wang, Zhiming
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supporting information
p. 184 - 198
(2021/09/20)
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- 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.
- Cooke, Maria Victoria,Laulhé, Sébastien,Pan, Lei,Spencer, Amara
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supporting information
(2021/11/01)
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- Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings
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Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.
- Martín, M. Trinidad,Marín, Mario,Maya, Celia,Prieto, Auxiliadora,Nicasio, M. Carmen
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supporting information
p. 12320 - 12326
(2021/08/09)
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- Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
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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
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supporting information
p. 6164 - 6168
(2021/08/16)
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- A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst
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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
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supporting information
p. 10820 - 10827
(2021/04/09)
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- A semiconducting supramolecular Co(ii)-metallohydrogel: an efficient catalyst for single-pot aryl-S bond formation at room temperature
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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
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supporting information
p. 17388 - 17394
(2019/12/02)
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- Generation of Aryl Radicals from Aryl Halides: Rongalite-Promoted Transition-Metal-Free Arylation
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A new and practical method for the generation of aryl radicals from aryl halides is reported. Rongalite as a novel precursor of super electron donors was used to initiate a series of electron-catalyzed reactions under mild conditions. These transition-metal-free radical chain reactions enable the efficient formation of C-C, C-S, and C-P bonds through homolytic aromatic substitution or SRN1 reactions. Moreover, the synthesis of antipsychotic drug Quetiapine was performed on gram scale through the described method. This protocol demonstrated its potential as a promising arylation method in organic synthesis.
- Yu, Fazhi,Mao, Runyu,Yu, Mingcheng,Gu, Xianfeng,Wang, Yonghui
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p. 9946 - 9956
(2019/09/04)
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- CuFe2O4 magnetic nanoparticle catalyzed odorless synthesis of sulfides using phenylboronic acid and aryl halides in the presence of S8
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CuFe2O4 magnetic nanoparticles were prepared, characterized and used as a magnetically recoverable nanocatalyst for the one-pot synthesis of phenyl aryl/heteroaryl/benzyl sulfides through the cross-coupling reaction of phenylboronic acid with aryl/heteroaryl/benzyl halides in the presence of S8 as a sulfur source in PEG400 as a reusable solvent at 80 °C. Also, the synthesis of symmetrical sulfides from aryl/heteroaryl halides using S8, KF and Cs2CO3 in PEG400 at 120 °C is described. The magnetic nanocatalyst was recycled up to 6 times with little loss of activity.
- Amiri, Kamran,Rostami, Amin,Rostami, Abed
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p. 7522 - 7528
(2016/09/09)
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- Disulfides as efficient thiolating reagents enabling selective bis-sulfenylation of aryl dihalides under mild copper-catalyzed conditions
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Selective bis-sulfenylation reactions of aryl dihalides have been achieved by copper-catalyzed C-S coupling reactions under mild conditions of refluxing EtOH (80 °C). Employment of disulfides as thiolating reagents enables the production of various bis(phenylthio)benzenes with excellent selectivity, and no products from mono C-S coupling are isolated. the Partner Organisations 2014.
- Liu, Yunyun,Wang, Hang,Zhang, Jida,Wan, Jie-Ping,Wen, Chengping
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p. 19472 - 19475
(2014/05/20)
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- Synthesis of dibenzothiophenes by pd-catalyzed dual C-H activation from diaryl sulfides
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Palladium-catalyzed dual C-H functionalization of diaryl sulfides to form dibenzothiophenes (DBTs) by oxidative dehydrogenative cyclization is reported. This protocol afforded various DBTs in moderate to good yields with tolerance of a wide variety of substrates. Benzo[1,2-b:4,5-b]bis[b]benzothiophene was successfully synthesized by this method, which was used as an organic semiconductor for field-effect transistors.
- Che, Rui,Wu, Zhiqing,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
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p. 7258 - 7261
(2014/06/23)
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- Efficient recyclable CuI-nanoparticle-catalyzed S-arylation of thiols with aryl halides on water under mild conditions
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CuI nanoparticles efficiently catalyzed the C-S cross coupling of aryl and alkyl thiols with aryl halides in the absence of ligands on water under mild conditions. A wide range of diaryl sulfides and aryl alkyl sulfides are synthesized in good to excellent yields utilizing this protocol. This procedure is particularly noteworthy given its mild conditions, avoiding the undesired formation of disulfides through oxidation of thiols. The recovery and successful reutilization of the catalyst is described. Furthermore, the directed synthesis of bisarylated product is presented. The Royal Society of Chemistry 2012.
- Xu, Hua-Jian,Liang, Yu-Feng,Zhou, Xin-Feng,Feng, Yi-Si
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supporting information; experimental part
p. 2562 - 2568
(2012/04/23)
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- Carbon-sulfur coupling reactions catalyzed by Pd-NHC complex
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The cross-coupling reaction of aryl halides with aliphatic or aromatic thiols catalyzed by (SIPr)Pd(Py)Clis reported. This Pd-N-heterocyclic carbene (NHC) complex shows good to excellent activities toward various deactivated electron-rich aryl halides and even with unactivated aryl chlorides in C-S coupling reactions. The reactions proceeded in good yields, broad scope, and high tolerance of functional groups. The Pd-NHC complex is stable and easily to synthesize, so it is an excellent candidate to replace Pd-organophosphanes commonly used in C-S coupling catalysis. Georg Thieme Verlag Stuttgart - New York.
- Shi, Yanhui,Cai, Zhengyuan,Guan, Pei,Pang, Guangsheng
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supporting information; experimental part
p. 2090 - 2096
(2011/10/09)
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- Synthesis of unsymmetrical sulfides using ethyl potassium xanthogenate and recyclable copper catalyst under ligand-free conditions
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The synthesis of unsymmetrical sulfides has been achieved in good to excellent yields with inexpensive ethyl potassium xanthogenate via cross-coupling reaction using recyclable CuO nanoparticles under ligand-free conditions.The copper oxide nanoparticles can be recovered and reused up to five cycles without loss of activity.
- Akkilagunta, Vijay Kumar,Kakulapati, Rama Rao
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supporting information; experimental part
p. 6819 - 6824
(2011/10/09)
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- Ligand-free highly effective iron/copper co-catalyzed formation of dimeric aryl ethers or sulfides
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Highly selective coupling of diiodoarenes with phenols or phenthiols can be performed by using a low-cost, benign character and readily available Fe/Cu catalytic system in the absence of ligands. It is noteworthy that the desired dimeric aryl ethers or sulfides could be obtained in high yields by coupling between diiodoarenes and phenols, or diphenols with aryl iodides. The Royal Society of Chemistry 2011.
- Qu, Xiaoming,Li, Tingyi,Zhu, Yan,Sun, Peng,Yang, Hailong,Mao, Jincheng
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supporting information; experimental part
p. 5043 - 5046
(2011/08/22)
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- 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
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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
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experimental part
p. 5989 - 5996
(2011/10/08)
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- Efficient copper-catalyzed S-arylation of thiols with aryl bromides and chlorides
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An efficient copper-catalyzed system for C-S cross-coupling of aromatic thiols with aryl bromides and chlorides has been developed using 1,2,3,4-tetrahydroquinoline-8-ol as a ligand. It is noteworthy that this method is proved to be especially effective for aryl bromides with electron-donating groups. By this protocol, a variety of thioethers as well as symmetrical and unsymmetrical bis-thioethers are obtained in excellent yields with an exceptional level of functional group tolerance and high chemoselectivity. Georg Thieme Verlag Stuttgart - New York.
- Li, Yaming,Li, Xiaoying,Wang, Huifeng,Chen, Tao,Xie, Yusheng
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supporting information; experimental part
p. 3602 - 3608
(2010/12/19)
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- MALDI-TOF/TOF CID study of poly(p-phenylene sulfide) fragmentation reactions
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A study involving the evaporation-grinding MALDI sample preparation method, MALDITOF/TOF CID, and Py-GC/MS is presented to examine the fragmentation mechanisms of poly(p-phenylene sulfide) (PPS). MALDI-TOF/TOF CID fragmentation studies yielded a wealth of information about the mass, structure (linear or cyclic), end-groups, and backbone modifications of the polymer. Additionally, Py-GC/MS experimental data are presented for comparison of the multimolecular free radical reactions in pyrolysis with the unimolecular fragmentation reactions of MS/MS.1,2 TOF/TOF CID results indicate that linear PPS undergoes random main chain fragmentation along the polymer backbone and preferentially fragments at bonds adjacent to dibenzothiophene and phenyl end-groups. Cyclic species produce fragment ions similar to linear species. However, the MS/MS precursor ions for cyclic PPS are, by far, the most intense peaks, while the precursor ions for linear species show relatively low intensity. CID fragmentation results are supported by Py-GC/MS data and are consistent with the proposed degradation mechanisms.
- Gies, Anthony P.,Geibel, Jon F.,Hercules, David M.
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experimental part
p. 952 - 967
(2011/10/08)
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- Recyclable iron/graphite catalyst for c-s cross coupling of thiols with aryl halides under ligand-free conditions
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A recyclable iron/graphite (Fe/Cg) catalyst for the efficient C-S cross-coupling of various iodoarenes with aromatic/aliphatic thiols has been developed under ligand-free conditions (26 examples, up to 99% yield). The catalyst can be easily recovered and recycled up to seven cycles without loss of activity. Georg Thieme Verlag Stuttgart.
- Akkilagunta, Vijay Kumar,Reddy, Vutukuri Prakash,Rao, Kakulapati Rama
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supporting information; experimental part
p. 1260 - 1264
(2010/07/05)
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- Efficient ligand-free copper-catalyzed C-S cross-coupling of thiols with aryl iodides using KF/Al2O3 as base
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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.
- Feng, Yi-Si,Li, Yuan-Yuan,Tang, Lin,Wu, Wei,Xu, Hua-Jian
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experimental part
p. 2489 - 2492
(2010/06/14)
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- p-Phenylene sulfide oligomers and their properties. Ar-S couplings mediated by copper or by fluorine substitutions
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A series of monodisperse p-phenylene sulfide oligomers were efficiently synthesized by using a bidirectional growth. A strategy combining Cu-catalyzed Ar-S couplings for small oligomers and fluorine aromatic substitutions by aryl thiolates for longer ones was put forward. The latter method is superior to Cu-catalyzed reactions for longer oligomers. Fluorine chemistry brings some new advantages such as solubility and reactivity. Qualitative crystallinity studies were reported according to the oligomer size and the functional series, by using a microscope equipped with a heating stage and a camera.
- Goyot, Olivier,Gingras, Marc
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scheme or table
p. 1977 - 1981
(2009/07/05)
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- Facile preparation of aryl sulfides catalyzed by PEG400 and nickel without solvent
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A variety of aryl sulfides were synthesized by aryl bromides with thiols, with PEG400 and nickel as catalysts under basic conditions in the absence of solvents. This article reported an easy and convenient method for formation of aryl-sulfur bonds. Copyright Taylor & Francis Group, LLC.
- Cao, Yu-Qing,Zhang, Zhan,Guo, Yan-Xin,Wu, Guo-Qiang
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p. 1325 - 1332
(2008/09/19)
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- Magnesium-Induced Copper-Catalyzed Synthesis of Unsymmetrical Diaryl Chalcogenide Compounds from Aryl Iodide via Cleavage of the Se-Se or S-S Bond
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The methodology for a copper-catalyzed preparation of diaryl chalcogenide compounds from aryl iodides and diphenyl dichalcogenide molecules is reported. Unsymmetrical diaryl sulfide or diaryl selenide can be synthesized from aryl iodide and PhYYPh (Y = S, Se) with a copper catalyst (CuI or Cu2O) and magnesium metal in one pot. This reaction can be carried out under neutral conditions according to an addition of magnesium metal as the reductive reagent. Furthermore, it is efficiently available for two monophenylchalcogenide groups generated from diphenyl dichalcogenide.
- Taniguchi, Nobukazu,Onami, Tetsuo
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p. 915 - 920
(2007/10/03)
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- CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands
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Novel mild conditions for the CuI-catalyzed coupling reactions of aryl iodides and bromides with aliphatic and aromatic thiols using amino acids as the ligand are reported.
- Deng, Wei,Zou, Yan,Wang, Ye-Feng,Liu, Lei,Guo, Qing-Xiang
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p. 1254 - 1258
(2007/10/03)
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- Ring-opening reactions of 5-(aryl)thianthrenium bromides with aryl thiolates
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A series of 5-(aryl)thianthrenium bromides (6a-e) with aryl (Ar) groups phenyl (a), p-tolyl (b), p-anisyl (c), p-chlorophenyl (d) and p-bromophenyl (e) was prepared by reaction of thianthrene 5-oxide with the appropriate Grignard reagent ArMgBr. Reactions of 6a-e with aryl thiolates (Ar′SNa, Ar′ = phenyl, p-tolyl and p-chlorophenyl, 7a-c) were carried out in MeCN at room temperature. Products from 6a-c were a small amount of arene [benzene (8a) and toluene (8b)], and substantial amounts of ArSAr′ (9), thianthrene (Th) and a trisulfide, namely a 2-(ArS)-2′-(Ar′S)-diphenyl sulfide (10). Products from reactions of 6d,e were smaller amounts of 9 and 10 but substantial amounts of 1,4-di(Ar′S)benzene (11) and a tetrasulfide (12a-c). The reactions that lead to products 9-12 are attributed to ligand coupling (LC) pathways in sulfuranes formed by attack of Ar′S- at the sulfonium S atom of 6. In the formation of 11 and 12 the halogen atom (CI, Br) is first displaced from 6d,e by Ar′S-, giving a new thianthrenium ion (14) from which sulfurane formation (15) follows. Products 10 and 12 result from opening of the thianthrenium ring of sulfuranes 13 and 15 through LC. Products were assayed with a combination of GC and isolation with TLC, and were identified with a combination of GC (authentic compounds), x-ray crystallography (10a), elemental analyses and high-resolution mass spectrometry. The reactions of 6 are compared with earlier reactions of 5-(alkoxy)-and 5-(alkyl)thianthrenium salts (1 and 2). Copyright
- Qian, Ding-Quan,Liu, Bo,Shine, Henry J.,Guzman-Jimenez, Ilse Y.,Whitmire, Kenton H.
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p. 139 - 147
(2007/10/03)
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- A novel synthesis of diaryl sulfides
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Reaction of diphenyl disulfide and aryl iodides or diiodides at high temperature affords phenyl aryl sulfides or bis(phenylthio)arenes in good yields. Thermolysis of dialkyl disulfide with aryl iodides yields only diaryl sulfides.
- Wang,Hay
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p. 5685 - 5686
(2007/10/02)
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- Monosubstitution versus Disubstitution in the SRN1 Reaction of Dihalobenzenes with Sulfanions. The Role of the Monosubstitution Product and of Its Anion Radical
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The competition between mono- and disubstitution of dihalobenzenes by a series of aromatic sulfanions, via the SRN1 reaction, is shown to involve two radical chains.The first one, recognized in earliest works, involves one branching point at the level of the monosubstituted product anion radical.Reoxidation of the latter via electron transfer to the parent dihalide affords the monosubstituted product.Conversely, the route to the disubstituted product is opened when cleavage of the carbon-halogen bond in the monosubstituted product anion radical occurs before the electron transfer takes place; the disubstitution product is then obtained in its reduced (anion radical) form.Reoxidation of the latter, to afford the neutral disubstituted product, may involve competitively the parent dihalide or the neutral monosubstituted product, depending on the electron affinity of the arylthio moiety.In the first case the electron transfer propagates the first chain; in the second a new chain leading to the disubstitution is activated.The role of the two imbricated chains, under photochemical conditions, and thus that of the monosubstitution product is discussed quantitatively on the basis of the pertinent rate constants determined by cyclic voltammetry.
- Amatore, C.,Beugelmans, R.,Bois-Choussy, M.,Combellas, C.,Thiebault, A.
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p. 5688 - 5695
(2007/10/02)
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- A CONVENIENT SRN1 SYNTHESIS OF AROMATIC NITRILES FROM DIAZONIUM SALTS VIA DIAZOSULFIDES
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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
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p. 4625 - 4634
(2007/10/02)
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- A MILD AND EFFICIENT SRN1 APPROACH TO DIARYL SULFIDES FROM ARENEDIAZONIUM TETRAFLUOROBORATES
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The reaction between arenediazonium tetrafluoroborates and sodium arenethiolates in Me2SO at 25 deg C represent an efficient access to diaryl sulfides.A number of evidences suggest the occurance of a radical, radical-anion SRN1 mechanism, the arenethiolate acting both as electron donor and as aryl-radical trapping nucleophile.Valuable improvements with respect to recent SRN1 syntheses of diaryl sulfides from haloarenes are represented, inter alia, by the compatibility of both electron-withdrawing and relasing substituents as well as by the intensivity to steric hindrance in the diazonium salt.When the arenediazonium ion bears another SRN1 leaving group (such as Cl, Br, or I) disubstitution products are predominantly formed.
- Petrillo, Giovanni,Novi, Marino,Garbarino, Giacomo,Dell'Erba, Carlo
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p. 4007 - 4016
(2007/10/02)
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- COPPER(1) CATALYSED AROMATIC NUCLEOPHILIC SUBSTITUTION: A MECHANISTIC AND SYNTHETIC COMPARISON WITH SRN1 REACTION
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Evidence is provided to support a mechanism for Cu(1) catalysed aromatic nucleophilic substitution via inner-sphere electron-transfer and a Cu(111) intermediate, and to show the synthetic potential for Cu(1) catalysis relative to the SRN1 reaction.
- Bowman, W. Russel,Heaney, Harry,Smith, Philip H. G.
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p. 5821 - 5824
(2007/10/02)
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