- A facile and convenient synthesis of 2-(arylthio)thiophenes, 2-(alkylthio)thiophene, and 2-(thiophenylthio)thiophene
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2-(Arylthio)thiophenes, 2-(alkylthio)thiophene, and 2-(thiophenylthio)thiophene were prepared in high yield by simply mixing 2-iodothiophene and aryl, alkyl, or thienyl thiols at room temperature without solvent, base, and/or catalyst.
- Sang, Bok Lee,Jong-In, Hong
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Read Online
- Photostimulated SRN1 Reactions of Halothiophenes with Benzenethiolate Ion in Acetonitrile
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The photostimulated reactions between benzenethiolate and 2-chloro-, 2-bromo-, 2-iodo-, and 3-bromothiophene in MeCN lead to rather complex product mixtures where the phenyl thienyl sulfide(ThSPh), the ipso-substitution product, represents the main component.The collected results agree well with the occurrence of an SRN1 chain pathway.As to the obtainable yield of sulfide, the main drawback is represented by the fragmentation into ThS- and Ph(radical) of the ThSPh radical anion, formeded either along the propagation cycle or by single-electron reduction of the sulfide itself.Optimization of the yield of ThSPh, although at the expense of the overall reaction rate, can be achieved by the employment of suitable electron acceptors.The overall reactivity orders (2-I > 2-Br > 2-Cl and 2-Br > 3-Br) are also discussed.
- Novi, Marino,Garbarino, Giacomo,Petrillo, Giovanni,Dell"Erba, Carlo
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Read Online
- Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
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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.
- Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
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supporting information
p. 8098 - 8103
(2021/10/25)
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- Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
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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.
- Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
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p. 10829 - 10837
(2021/07/28)
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- Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols
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Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of the C(aryl)-C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)-C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)-C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohol conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)-C(OH) bonds in its linkages.
- Chen, Bingfeng,Han, Buxing,Liu, Mingyang,Meng, Qinglei,Song, Jinliang,Zhang, Pei,Zhang, Zhanrong
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p. 7634 - 7640
(2020/08/14)
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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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- Method for synthesizing asymmetric sulfide from molecular oxygen oxidation water phase under catalysis of water-soluble transition metal compound
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Aiming at problems that in the prior art organic solvent pollution can be caused and a great number of reaction byproducts are generated when asymmetric sulfides are prepared, the invention disclosesa method for synthesizing an asymmetric sulfide from a molecular oxygen oxidation water phase under catalysis of a water-soluble transition metal compound. The method comprises the following steps: dispersing a sulfydryl compound and a hydrazine compound as substrates in a mole ratio of 1:1 into an alkali solution, and at 40-100 DEG C, in the presence of oxygen, and with a water-soluble transitionmetal compound as a catalyst, stirring to carry out reactions, thereby obtaining the asymmetric sulfide. By adopting the method, molecular oxygen is adopted as an oxidant, and water is adopted as a solvent, so that an organic solvent is avoided, a high yield can be achieved, and the problem of byproducts can be generally avoided.
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Paragraph 0091
(2019/07/29)
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- Surfactant-Type Catalyst for Aerobic Oxidative Coupling of Hydrazine with Thiol in Water
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A series of PEG-functionalized nitrogen ligands were developed to conduct an aerobic oxidative cross-coupling reaction between alkyl- or aryl-hydrazines with thiols in water. This surfactant-type catalyst enables high efficiencies and selectivities, while tolerating a large variety of functional groups. The mother liquor is still catalytically active after five runs.
- Ren, Xuanhe,Tang, Shanyu,Li, Longjia,Li, Jiao,Liang, Helong,Li, Ganzhong,Yang, Guanyu,Li, Heng,Yuan, Bingxin
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p. 8683 - 8690
(2019/07/08)
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- Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity
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A simple and efficient approach of C-S cross-coupling of a wide variety of (hetero)aryl thiols and (hetero)aryl halides under mild conditions, mostly at room temperature, catalyzed by well-defined singlet diradical Ni(II) catalysts bearing redox noninnocent ligands is reported. Taking advantage of ligand centered redox events, the high-energetic Ni(0)/Ni(II) or Ni(I)/Ni(III) redox steps were avoided in the catalytic cycle. The cooperative participation of both nickel and the coordinated ligands during oxidative addition/reductive elimination steps allowed us to perform the catalytic reactions under mild conditions.
- Sikari, Rina,Sinha, Suman,Das, Siuli,Saha, Anannya,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
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p. 4072 - 4085
(2019/04/01)
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- Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts
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A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest.
- Liu, Chengwei,Szostak, Michal
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p. 2130 - 2133
(2018/03/06)
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- Palladium- and Nickel-Catalyzed Decarbonylative C-S Coupling to Convert Thioesters to Thioethers
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This Letter describes the development of a catalytic decarbonylative C-S coupling reaction that transforms thioesters into thioethers. Both Pd- and Ni-based catalysts are developed and applied to the construction of diaryl, aryl alkyl, and heterocycle-containing thioethers.
- Ichiishi, Naoko,Malapit, Christian A.,Wo?niak, Aukasz,Sanford, Melanie S.
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supporting information
p. 44 - 47
(2018/01/17)
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- Nickel Phosphite/Phosphine-Catalyzed C-S Cross-Coupling of Aryl Chlorides and Thiols
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A method for the coupling of aryl chlorides and thiophenols using an air-stable nickel(0) catalyst is described. This thioetherification procedure can be effectively applied to a range of electronically diverse aryl/heteroaryl chlorides without more expensive metal catalysts such as palladium, iridium, or ruthenium. This investigation also illustrates both, a variety of thiol coupling partners and, in certain cases, the use of Cs2CO3.
- Jones, Kieran D.,Power, Dennis J.,Bierer, Donald,Gericke, Kersten M.,Stewart, Scott G.
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supporting information
p. 208 - 211
(2018/01/17)
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- CuI promoted sulfenylation of organozinc reagents with arylsulfonyl chlorides
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A CuI promoted sulfenylation of organozinc reagents with arylsulfonyl chlorides/PPh3 has been explored. This reaction proceeded smoothly through an alkyl/aryl radical (generated from organometallics) under mild conditions and produced the desired sulfide products in excellent yields.
- Fu, Ying,Su, Yuhu,Xu, Qin-Shan,Du, Zhengyin,Hu, Yulai,Wang, Ke-Hu,Huang, Danfeng
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p. 6018 - 6022
(2017/02/05)
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- Synthesis of o-Aryloxy Triarylsulfonium Salts via Aryne Insertion into Diaryl Sulfoxides
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The aryne insertion into "S-O" bond has been validated recently. This technology is elusively applied to the synthesis of thioethers. In contrast to the reported cases, the reaction described furnished o-aryloxy triarylsulfonium salts, in lieu of thioethe
- Li, Xiaojin,Sun, Yan,Huang, Xin,Zhang, Lei,Kong, Lichun,Peng, Bo
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supporting information
p. 838 - 841
(2017/02/26)
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- Ferromagnetic nanoparticle-supported copper complex: A highly efficient and reusable catalyst for three-component syntheses of 1,4-disubstituted 1,2,3-triazoles and C–S coupling of aryl halides
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A new nanocatalyst was synthesized by immobilization of 4′-(4-hydroxyphenyl)-2,2′:6′,2″-terpyridine/CuI complex on ferromagnetic nanoparticles through a surface modification (FMNPs@SiO2-TPy-Cu). This heterogeneous catalyst was characterized using various techniques including Fourier transform infrared and energy-dispersive X-ray spectroscopies, transmission and scanning electron microscopies, X-ray diffraction, vibrating sample magnetometry and thermogravimetric analysis. The resulting nanocatalyst presented excellent catalytic activity for the regioselective syntheses of 1,4-disubstituted 1,2,3-triazoles and thioethers. The thermally and chemically stable, benign and economical catalyst was easily recovered using an external magnet and reused in at least five successive runs without an appreciable loss of activity.
- Khodaei, Mohammad Mehdi,Bahrami, Kiumars,Meibodi, Farhat Sadat
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- Metal-free C-H thioarylation of arenes using sulfoxides: A direct, general diaryl sulfide synthesis
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Metal-free C-H thioarylation of arenes and heteroarenes using methyl sulfoxides constitutes a general protocol for the synthesis of high value diaryl sulfides. The coupling of arenes and heteroarenes with in situ activated sulfoxides is regioselective, uses readily available starting materials, is operationally simple, and tolerates a wide range of functional groups.
- Fernández-Salas, José A.,Pulis, Alexander P.,Procter, David J.
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p. 12364 - 12367
(2016/10/22)
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- Ligand-free copper-catalyzed synthesis of asymmetrical thioethers by coupling aryl or alkyl halides using an acetyl thiourea precursor in wet polyethylene glyol (PEG 400)
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Asymmetrical diaryl or aryl alkyl thioethers can be prepared in good to excellent yields by coupling the appropriate aryl iodides and aryl or alkyl bromines using acetyl thiourea as a thiolprecursor, Cu2O as a catalyst, KOH as a base, and PEG 400-H2O as a solvent under ligand-free conditions.
- Zhang, Baohua,Shi, Lanxiang,Guo, Ruixia,Wang, Juan
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p. 561 - 566
(2015/05/20)
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- Copper nanopowder catalyzed cross-coupling of diaryl disulfides with aryl iodides in PEG-400
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An eco-friendly thiolation via diaryl disulfides and aryl iodides under ligand-free conditions is reported. With copper nanopowder as catalyst and PEG-400 as solvent, a variety of unsymmetrical diaryl sulfides are synthesized in good to excellent yields. The process is free from foul-smelling and unstable thiols and the copper nanopowder-PEG-400 catalytic system can be directly reused for four repetitive cycles.
- Wu, Xiang-Mei,Yan, Guo-Bing
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supporting information
p. 537 - 542
(2015/04/27)
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- An efficient protocol for the carbon-sulfur cross-coupling of sulfenyl chlorides with arylboronic acids using a palladium catalyst
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An efficient protocol for carbon-sulfur bond formation is developed, which involves the cross-coupling of sulfenyl chlorides and arylboronic acids catalyzed by a novel palladium-Schiff base complex. Good to high product yields, short reaction times, and mild reaction conditions are important features of this new method. Georg Thieme Verlag Stuttgart · New York.
- Gogoi, Prasanta,Kalita, Mukul,Barman, Pranjit
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p. 866 - 870
(2014/04/03)
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- Palladium-catalyzed C-S bond formation by using N-amido imidazolium salts as ligands
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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.
- Byeun, Aleum,Baek, Kyungkyu,Han, Min Su,Lee, Sunwoo
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p. 6712 - 6715
(2013/11/19)
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- A new family of nucleophiles for photoinduced, copper-catalyzed cross-couplings via single-electron transfer: Reactions of thiols with aryl halides under mild conditions (O C)
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Building on the known photophysical properties of well-defined copper-carbazolide complexes, we have recently described photoinduced, copper-catalyzed N-arylations and N-alkylations of carbazoles. Until now, there have been no examples of the use of other families of heteroatom nucleophiles in such photoinduced processes. Herein, we report a versatile photoinduced, copper-catalyzed method for coupling aryl thiols with aryl halides, wherein a single set of reaction conditions, using inexpensive CuI as a precatalyst without the need for an added ligand, is effective for a wide range of coupling partners. As far as we are aware, copper-catalyzed C-S cross-couplings at 0 C have not previously been achieved, which renders our observation of efficient reaction of an unactivated aryl iodide at -40 C especially striking. Mechanistic investigations are consistent with these photoinduced C-S cross-couplings following a SET/radical pathway for C-X bond cleavage (via a Cu(I)-thiolate), which contrasts with nonphotoinduced, copper-catalyzed processes wherein a concerted mechanism is believed to occur.
- Uyeda, Christopher,Tan, Yichen,Fu, Gregory C.,Peters, Jonas C.
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supporting information
p. 9548 - 9552
(2013/07/19)
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- Chan-lam-type s-arylation of thiols with boronic acids at room temperature
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In this work, an efficient CuSO4-catalyzed S-arylation of thiols with aryl and heteroaryl boronic acids at room temperature is established. This catalytic system can tolerate a wide variety of thiols and arylboronic acids in the presence of only 5 mol % of CuSO4 as the catalyst and inexpensive 1,10-phen?H2O as the ligand. Moreover, this catalytic system used environment-friendly solvent (EtOH) and oxidant (oxygen).
- Xu, Hua-Jian,Zhao, Yong-Qiang,Feng, Teng,Feng, Yi-Si
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experimental part
p. 2878 - 2884
(2012/05/04)
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- Efficient 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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- Simple and efficient copper-catalyzed S-arylation of diaryl disulfides with triarylbismuthanes under aerobic conditions
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Novel and simple copper-catalyzed C(aryl)-S bond formation of diaryl disulfides with bismuth reagents is described. Reactions of diaryl disulfides with triarylbismuthanes in the presence of CuOAc (10 mol %) and 1,10-phenanthroline (10 mol %) under aerobic conditions led to the formation of unsymmetrical diaryl sulfides in satisfactory yields. The reaction is atom-economic and all three aryl groups of the triarylbismuthanes and both sulfanyl groups of the diaryl disulfides could be transferred to the coupling products.
- Yasuike, Shuji,Nishioka, Motokazu,Kakusawa, Naoki,Kurita, Jyoji
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experimental part
p. 6403 - 6406
(2011/12/22)
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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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- 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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- 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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- 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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- Regiospecific reductive elimination from diaryliodonium salts
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(Figure Presented) Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent maingroup and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.
- Wang, Bijia,Graskemper, Joseph W.,Qin, Linlin,DiMagno, Stephen G.
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supporting information; experimental part
p. 4079 - 4083
(2010/08/07)
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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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- A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides
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The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in excellent yields, broad scope, high tolerance of functional groups, and with turnover numbers that exceed those of previous catalysts by 2 or 3 orders of magnitude. These couplings of bromo- and iodoarenes are more efficient than the corresponding reactions of chloroarenes and could be conducted with less catalyst loading and/or milder reaction conditions. Consequently, limitations regarding scope and functional group tolerance previously reported in the coupling of aryl chlorides are now overcome.
- Fernandez-Rodriguez, Manuel A.,Hartwig, John F.
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experimental part
p. 1664 - 1672
(2009/07/17)
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- Efficient C-S cross coupling catalyzed by Cu2O
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A protocol for the copper-catalyzed C-S bond formation between aryl, alkyl, or heteroaryl thiols and aryl or heteroaryl halides is reported. The reaction is catalyzed by Cu2O which shows the highest catalytic activity with ethyl 2-oxocyclohexanecarboxylate ligand in DMSO at 80 °C. The corresponding coupling products are obtained with good to excellent yields under relatively mild reaction conditions with good chemoselectivity and functional group tolerance.
- Xu, Hua-Jian,Zhao, Xiao-Yang,Deng, Jin,Fu, Yao,Feng, Yi-Si
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experimental part
p. 434 - 437
(2009/05/11)
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- Ligand-free C-S bond formation catalyzed by copper(I) oxide
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An efficient ligand-free Cu2O-catalyzed C-S bond-formation reaction was developed. A large number of diaryl sulfides and alkylaryl sulfides could be rapidly assembled using this new reaction protocol. Georg Thieme Verlag Stuttgart.
- Xu, Hua-Jian,Zhao, Xiao-Yang,Fu, Yao,Feng, Yi-Si
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experimental part
p. 3063 - 3067
(2009/07/04)
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- Methods for formation of aryl-sulfur and aryl-selenium compounds using copper(I) catalysts
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A mild, palladium-free synthetic protocol for the cross-coupling reaction of vinyl or aryl iodides and thiols or selenols using, in certain embodiments, 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 ° C. A variety of vinyl/aryl sulfides and vinyl/aryl selenides can be synthesized in excellent yields from readily available iodides and thiols or selenols.
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Page/Page column 7-8; 24
(2008/06/13)
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- Palladium-catalyzed coupling reaction of diaryl dichalcogenide with aryl bromide leading to the synthesis of unsymmetrical aryl chalcogenide
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An efficient cross-coupling reaction of diphenyl disulfide or diselenide with substituted aryl bromides using PdCl2(dppf) and zinc has been developed. This method gave functionalized unsymmetrical aryl sulfides and selenides in good to excellent yields under neutral conditions. Georg Thieme Verlag Stuttgart.
- Fukuzawa, Shin-Ichi,Tanihara, Daisuke,Kikuchi, Satoshi
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p. 2145 - 2147
(2008/02/05)
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- Copper- and palladium-containing perovskites: Catalysts for the Ullmann and Sonogashira reactions
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The utility of perovskite-based materials in organic synthesis is explored through examination of a series of copper- and palladium-containing perovskites in Ullmann and Sonogashira type reactions. La0.9Ce 0.1Co0.6Cu0.4O3 is identified as an effective catalyst for the synthesis of a range of biaryl ether and thioether functionalities, whilst a Cu- and Pd-containing perovskite is effective in the Sonogashira reaction. These results suggest that perovskites may be useful leads in the search for new catalysts and reagents for organic synthesis.
- Lohmann, Sophie,Andrews, Stephen P.,Burke, Brenda J.,Smith, Martin D.,Attfield, J. Paul,Tanaka, Hirohisa,Kaneko, Kimiyoshi,Ley, Steven V.
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p. 1291 - 1295
(2007/10/03)
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- Highly regioselective nucleophilic carbon - Carbon bond formation on furans and thiophenes initiated by pummerer-type reaction
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(Chemical Equation Presented) The reactions of (phenylsulfinyl)furans or -thiophenes with carbon nucleophiles in the presence of trifluoroacetic anhydride allowed the nucleophilic installation of carbon functional groups on the furan and thiophene nuclei
- Akai, Shuji,Kawashita, Norihito,Satoh, Hideharu,Wada, Yasufumi,Kakiguchi, Keisuke,Kuriwaki, Ikumi,Kita, Yasuyuki
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p. 3793 - 3796
(2007/10/03)
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- A general method for the formation of aryl-sulfur bonds using copper(I) catalysts.
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[reaction: see text] We report a mild, palladium-free synthetic protocol for the cross-coupling reaction of aryl iodides and thiols using 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 degrees 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.
- Bates, Craig G,Gujadhur, Rattan K,Venkataraman
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p. 2803 - 2806
(2007/10/03)
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- Pharmaceutical compounds
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A pharmaceutical compound of the formula STR1 in which R1 is halo-C1-10 alkyl, C1-10 alkylthio, halo-C1-10 alkylthio or optionally substituted phenylthio, R2 is hydrogen or C1-4 alkyl, Rsu
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