- Efficient synthesis of diaryl sulfides by copper-catalysed coupling of aryl halides and thioacetate in water
-
A simple economical, and highly efficient catalytic system for the synthesis of diaryl sulfides by a copper-catalysed coupling of aryl halides and thioacetate in water has been developed. A variety of aryl halides reacted with thioacetate to give the desired products in high yields up to 95%. The present catalysis protocol tolerated a wide range of functional groups, including amino, fluoro, and carboxyl moieties.
- Zhang, Yimin,Liu, Li,Chen, Junmin
-
-
Read Online
- Diamine compound containing sulfoxide-based bridge chain as well as synthesis method and application of diamine compound containing sulfoxide-based bridge chain
-
The invention provides a diamine compound containing a sulfoxide-based bridge chain as well as a synthesis method and application of the diamine compound containing the sulfoxide-based bridge chain. Sulfoxide diamine synthesized by the method contains a sulfoxide-based bridge chain structure. The synthesis method has the characteristics of simple synthetic route, mild reaction conditions, highly available reaction raw material source, low cost, few organic solvent use types, capability of reducing environmental pollution to the greatest extent and the like. The diamine compound provided by theinvention has a sulfoxide group in structure; and in the synthesis of a polymer material, the diamine compound can improve the light transmittance of the material, increase the heat resistance and reduce the dielectric constant and water absorption of the material, and therefore, the diamine compound is suitable for synthesizing flexible transparent polyimide or polyamide and other films.
- -
-
Paragraph 0032; 0034
(2020/10/21)
-
- DIAMINE COMPOUND, AND POLYIMIDE PRECURSOR AND POLYIMIDE FILM PREPARED BY USING THE SAME
-
The present invention disclosed a novel diamine compound including a structure in which a phenylene linker (L) connecting an intramolecular imide ring and the imide ring is bonded to a phenyl ring substituted with -NH-(C=O)- or -O-(C=O)-. A polyimide film prepared by polymerizing the novel diamine compound has not only improved mechanical and thermal properties, but also an excellent refractive index.COPYRIGHT KIPO 2021
- -
-
Paragraph 0271; 0272; 0275; 0276
(2020/11/03)
-
- Solid-State C-S Coupling in Nickel Organochalcogenide Frameworks as a Route to Hierarchical Structure Transfer to Binary Nanomaterials
-
In this work, the transfer of the flexible and easily tunable hierarchical structure of nickel organochalcogenides to different binary Ni-based nanomaterials via selective coupling of organic units was developed. We suggested the use of substituted aryl groups in organosulfur ligands (SAr) as traceless structure-inducing units to prepare nanostructured materials. At the first step, it was shown that the slight variation of the type of SAr units and synthetic procedures allowed us to obtain nickel thiolates [Ni(SAr)2]n with diverse morphologies after a self-assembly process in solution. This feature opened the way for the synthesis of different nanomaterials from a single type of precursor using the phenomenon of direct transfer of morphology. This study revealed that various nickel thiolates undergo selective C-S coupling under high-temperature conditions with the formation of highly demanding nanostructured NiS particles and corresponding diaryl sulfides. The in situ oxidation of the formed nickel sulfide in the case of reaction in an air atmosphere provided another type of valuable nanomaterial, nickel oxide. The high selectivity of the transformation allowed the preservation of the initial organochalcogenide morphologies in the resulting products.
- Ananikov, Valentine P.,Degtyareva, Evgeniya S.,Galushko, Alexey S.,Kashin, Alexey S.
-
-
- Flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines
-
A flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines with thiols under mild reaction conditions is presented for the first time. This metal-free reaction provides an atom-economic pathway to prepare various aryl sulfides with outstanding functional group compatibility. Moreover, it consumes molecular oxygen as the only terminal oxidant and produces environmentally-friendly H2O as the only byproduct.
- Jiang, Xinpeng,Shen, Zhifeng,Zheng, Cong,Fang, Liyun,Chen, Keda,Yu, Chuanming
-
supporting information
(2020/07/24)
-
- Magnetically recoverable ferromagnetic 3D hierarchical core-shell Fe3O4@NiO/Co3O4 microspheres as an efficient and ligand-free catalyst for C–S bond formation in poly (ethylene glycol)
-
A simple and efficient protocol for the synthesis of diaryl thioethers from the reaction of thiourea with a wide variety of aryl halides, including aryl iodides, aryl bromides and aryl chlorides in the presence of 3D hierarchical core-shell Fe3O4@NiO/Co3O4 microspheres has been described. This reaction enables the one-pot synthesis of diaryl thioethers in good to high yields using a non-toxic and magnetically separable catalyst in PEG-400 as an eco-friendly, safe, inexpensive and thermally stable solvent. Magnetic separation and reusability of catalyst for eight times without any significant loss of activity, the use of a commercially available, eco-friendly, cheap and chemically stable sulfur transfer agent and solvent, operational simplicity, environmentally benign, easier work-up procedure and cost efficiency make this method a promising candidate for potential applications in some organic reactions. The catalytic activity of Fe3O4@NiO/Co3O4 as a novel and inexpensive catalyst was investigated in the C-S cross coupling reaction.
- Vatandoust Namanloo, Ahad,Akhlaghinia, Batool,Mohammadinezhad, Arezou
-
p. 446 - 461
(2020/05/13)
-
- Method for synthesis of diaryl thioether compound without transition metal catalysis
-
The invention discloses a method for synthesis of a diaryl thioether compound without transition metal catalysis. The method includes: in the presence of a riboflavin catalyst, an iodine source, and an oxidant, reacting a compound shown as formula (1) or a compound shown as formula (4) with a compound shown as formula (2) in a solvent at 30-100DEG C for 1-40h, and subjecting the reaction solutionto post-treatment to obtain the diaryl thioether compound shown as formula (3) or formula (5). The reaction equation is shown as the specification, in the formula (1)-formula (5), R1 is selected fromC1-C4 alkyl, aryl, C1-C4 alkoxy, halogen, halogen-substituted C1-C4 alkyl, aryl, nitro, cyano, amino, or heterocyclic mercaptan; R2, R3, and R4 are independently selected from one of H, C1-C4 alkyl, halogen-substituted C1-C4 alkyl, and aryl respectively; R5 and R6 are independently selected from C1-C4 alkyl respectively, and Y represents element O. The method provided by the invention uses a riboflavin catalyst to replace a transition metal to synthesize the diaryl thioether compound, and has the advantages of green reaction, mild conditions, good substrate universality, high yield and the like.
- -
-
Paragraph 0040-0042
(2019/11/28)
-
- C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
-
An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.
- Xuan, Maojie,Lu, Chunlei,Lin, Bo-Lin
-
-
- CuI anchored onto mesoporous SBA-16 functionalized by aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide (SBA-16/GPTMS-TSC-CuI): A heterogeneous mesostructured catalyst for: S -arylation reaction under solvent-free conditions
-
Herein, we report the novel synthesis of CuI anchored onto a cage-like mesoporous material (SBA-16), which was successfully functionalized by aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide (SBA-16/GPTMS-TSC-CuI) into an efficient and highly recyclable heterogeneous catalyst. The as-synthesized mesostructured catalyst (SBA-16/GPTMS-TSC-CuI) was comprehensively characterized by different techniques, namely, FT-IR, FIR, SAXRD, XRD, XPS, BET, TEM, FE-SEM, EDX, EDX mapping, TGA, ICP-OES, and CHNS analyses. SBA-16 with a unique "super-cage" structure efficiently controlled the formation of dispersed organic and metal species in the mesoporous channels. These confined nanoparticles with a narrow particle size distribution (3-7 nm) exhibited excellent catalytic activity in the S-arylation reaction without necessitating the use of toxic solvents and/or expensive metal catalysts. Interestingly, the mesoporous catalyst was extremely stable under the reaction conditions and could be easily separated by a simple filtration process and reused for at least seven recycle runs (without any appreciable loss in catalytic activity). Due to the inimitable structure of the abovementioned mesostructured catalyst, the C-S coupling products of aryl halides with S8/thiourea under solvent-free conditions were obtained in good to excellent yields in remarkably reduced reaction times in comparison to those reported in earlier studies.
- Ghodsinia, Sara S.E.,Akhlaghinia, Batool
-
p. 3029 - 3049
(2019/06/17)
-
- A novel heterogeneous nanocatalyst: 2-Methoxy-1-phenylethanone functionalized MCM-41 supported Cu(II) complex for C-S coupling of aryl halides with thiourea
-
An environmentally friendly copper-based catalyst supported on 2-Methoxy-1-phenylethanone functionalized MCM-41 was prepared and characterized by FT-IR, FE-SEM, TEM, XRD, EDX, BET and ICP techniques. The catalyst was applied for the C?S cross-coupling reaction of aryl halides with thiourea. Corresponding products were produced in good yields in aerobic conditions. The catalyst could be recovered and recycled for several times.
- Hajipour, Abdol R.,Fakhari, Farzaneh,Nabi Bidhendi, Gholamreza
-
-
- Ligand-free copper-catalysed direct synthesis of diaryl sulfides and diaryl disulfides in wet poly(ethylene glycol)
-
An improved protocol has been developed for the one-pot CuI-catalysed preparation of symmetric diaryl sulfides from their available aryl halides in the presence of thiourea as sulfur transfer agent and in the absence of both ligand and organic solvent. This catalytic system was also used for the high-yielding preparation of diaryl disulfides in the presence of C2Cl6 as oxidant.
- Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis
-
-
- Highly efficient and reusable polystyrene-supported copper(II) catalytic system for S-arylation of potassium thiocyanate by aryl halides in water
-
An inexpensive, efficient and environmentally friendly copper(II) catalyst supported on polystyrene was successfully synthesized and used as a heterogeneous catalyst for S-arylation of potassium thiocyanate by aryl halides. Also this catalyst could be recovered and reused several times without any noticeable decrease in its catalytic activity. Copyright
- Hajipour, Abdol R.,Jajarmi, Saeideh
-
p. 566 - 570
(2016/07/16)
-
- Selective synthesis of organic sulfides or disulfides by solvent exchange from aryl halides and KSCN catalyzed by NiCl2·6H2O
-
A method for selective synthesis of symmetric sulfides or disulfides from the reaction of aryl halides with KSCN by solvent exchange is introduced. Aryl halides were selectively converted to the symmetric disulfides or sulfides in high yields when they are treated with KSCN in the presence of NiCl2·6H2O and DMAP at 140?°C in DMF or poly ethylene glycol (PEG-200) respectively.
- Abbasi, Mohammad,Nowrouzi, Najmeh,Latifi, Hadis
-
p. 112 - 117
(2016/09/07)
-
- Thiol-free route to diaryl sulfides by Cu catalyzed coupling of sodium thiosulfate with aryl halides
-
A method for the synthesis of diaryl sulfides from aryl halides in polyethylene glycol was reported. Inodorous Na2S2O3·5H2O, which is readily available as a stable salt, is an effective source of sulfur in the presence of CuI as catalyst.
- Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis
-
p. 1550 - 1554
(2016/10/04)
-
- Fe-Cu catalyzed synthesis of symmetrical and unsymmetrical diaryl thioethers using 1,3-benzoxazole-2-thiol as a sulfur surrogate
-
An efficient Fe-Cu catalyzed approach is herein developed using 1,3-benzoxazole-2-thiol as a thiol surrogate for the synthesis of symmetrical and unsymmetrical diaryl thioethers. This method provides an odorless and inexpensive strategy which can be applied to various aryl and nitrogen containing aryl halides in moderate to excellent yields up to 90%.
- Tber,Hiebel,El Hakmaoui,Akssira,Guillaumet,Berteina-Raboin
-
p. 72030 - 72036
(2016/08/09)
-
- Highly efficient and magnetically separable nano-CuFe2O4 catalyzed S-arylation of thiourea by aryl/heteroaryl halides
-
The non-toxic and magnetically separable nano-CuFe2O4 catalyzed synthesis of symmetrical aryl sulfides by the reaction of thiourea with a wide variety of aryl halides, including aryl chlorides has been reported. Excellent yields of products have been obtained under ligand-free conditions and without the use of any expensive catalyst, such as palladium.
- Hajipour, Abdol R.,Karimzadeh, Morteza,Azizi, Ghobad
-
p. 1382 - 1386
(2015/02/19)
-
- CuI-catalyzed, symmetrical diaryl sulfides synthesis from aryl halides in the presence of KF/Al2O3: Using thiourea and thiosemicarbazide as sulfur donor sources
-
A convenient one-pot synthetic method is described for the synthesis of symmetrical diaryl sulfides via CuIcatalyzed cross-coupling reactions of various aryl halides and thiosemicarbazide (thiourea) in the presence of KF/Al 2O3.
- Soleiman-Beigi, Mohammad,Alikarami, Mohammad,Mohammadi, Fariba,Izadi, Azadeh
-
p. 622 - 625
(2013/12/04)
-
- Copper oxide nanoparticles supported on graphene oxide-Catalyzed S-arylation: An efficient and ligand-free synthesis of aryl sulfides
-
Copper oxide nanoparticles that are supported on graphene oxide as a catalytic system have been utilized for ligand-free and solvent-free C-S cross-coupling reactions with weak bases such as tri- ethylamine. Symmetrical/unsymmetrical aryl sulfides have been synthesized by the coupling of different aryl halides with aromatic as well as aliphatic sulfides. Surprisingly, aryl chlorides also well reacted with different types of sulfides in the presence of dimethyl sulfoxide and cesium carbonate. Besides, this catalytic system is suitable for the synthesis of phenothiazines via cascade C-S and C-N cross-coupling of ortho-dihalides and ortho-aminobenzothiazoles. In addition, this alternative approach is extremely useful for the synthesis of a variety of symmetrical diaryl sulfides by using thiourea as a sulfur source that is devoid of the foul smell of thiols. Indeed, the calculated E-factor value of our present protocol is 2.52. Furthermore, this protocol is particularly attractive as an environmentally benign and practical method for the synthesis of different aryl sulfides. Moreover, the heterogeneous catalytic system described in this process represents not only a greener approach but retains its significant activity for up to six catalytic cycles.
- Kamal, Ahmed,Srinivasulu, Vunnam,Murty,Shankaraiah, Nagula,Nagesh, Narayana,Reddy, T. Srinivasa,Subba Rao
-
p. 2297 - 2307
(2013/10/01)
-
- Sulfoximine- and sulfilimine-based DAPSON analogues; Syntheses and bioactivities
-
Sulfoximine- and sulfilimine-based diamino-diphenyl sulfone (DAPSON) analogues have been prepared and their COX-1 and COX-2 inhibition potencies as well as LTBand TNF binding properties were studied. Furthermore, their antiproliferative activities on cancer cell growth were investigated. Neither compounds showed significant bioactivities. Copyright
- Chen, Xiao Yun,Buschmann, Helmut,Bolm, Carsten
-
supporting information
p. 2808 - 2810
(2013/02/22)
-
- Efficient copper(I)-catalyzed S-arylation of KSCN with aryl halides in PEG-400
-
A simple and efficient protocol for CuI-catalyzed C-S bond formation of aryl halides with KSCN to symmetrical diaryl sulfides was reported in PEG-400 without any other additives. A variety of aryl halides were converted to the corresponding diaryl sulfides in good to excellent yields. The present procedure tolerated a variety of functional groups and the steric hindrance of ortho-substituents on aryl halides did not affect the outcome.
- Li, Xiaokang,Yuan, Tangjun,Chen, Junmin
-
experimental part
p. 651 - 655
(2012/05/05)
-
- Efficient copper-catalyzed double S-arylation of aryl halides with sodium sulfide in PEG-400
-
An efficient copper-catalyzed double S-arylation of sodium sulfide with aryl halides in PEG-400 has been developed. With CuI as a catalyst and PEG-400 as a solvent, a range of electron-withdrawing or electron-donating aryl iodides and aryl bromides were found to be applicable to the environmentally benign system. The present procedure is mild and tolerant of a variety of functional groups and the steric hindrance of ortho-substituents on aryl halides did not affect the outcome of good to excellent yields. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Chen, Junmin,Zhang, Yimin,Liu, Li,Yuan, Tangjun,Yi, Fei
-
p. 1284 - 1290
(2012/11/07)
-
- A highly efficient method for the copper-catalyzed selective synthesis of diaryl chalcogenides from easily available chalcogen sources
-
An efficient protocol for copper-catalyzed C-S or C-Se bond formation between aryl iodides and easily available chalcogen sources leading to diaryl chalcogenides is reported. A variety of symmetrical diaryl sulfides and diaryl selenides were synthesized in good to excellent yields. Unsymmetrical diaryl sulfides were also obtained in moderate yields from two different aryl iodides by a one-pot tandem process. This strategy was further successfully utilized for the synthesis of 2-phenylbenzo[b]thiophene and of [1]benzothieno[3,2-b] benzothiophene. A new Cu-catalyzed one-pot approach for the selective synthesis of symmetrical diaryl chalcogenides and unsymmetrical diarylsulfides with use of Na2S or Se as chalcogen sources has been developed. Copyright
- Li, Yaming,Nie, Caiping,Wang, Huifeng,Li, Xiaoying,Verpoort, Francis,Duan, Chunying
-
experimental part
p. 7331 - 7338
(2012/01/06)
-
- Copper oxide nanoparticles catalyzed synthesis of aryl sulfides via cascade reaction of aryl halides with thiourea
-
Recyclable copper oxide nanoparticles catalyzed simple and highly efficient protocol for the synthesis of symmetrical aryl sulfides was developed by the cross-coupling of aromatic halides with inexpensive and commercially available thiourea which was used as an effective sulfur surrogate. The present cross-coupling protocol of thiourea, via cascade reaction with various substituted aryl halides, producing desired aryl sulfides, has an added advantage of avoiding foul-smelling thiols.
- Reddy, K. Harsha Vardhan,Reddy, V. Prakash,Shankar,Madhav,Anil Kumar,Nageswar
-
supporting information; experimental part
p. 2679 - 2682
(2011/06/19)
-
- Ligand-free palladium-catalyzed C-S coupling reactions using water as solvent and microwaves
-
Herein we demonstrate for the first time a rapid and efficient method for the synthesis of aryl sulfides by the direct substitution reaction of aromatic thiols with aryl halides using water as solvent under microwave irradiation. This procedure offers a high yield in shorter reaction time as compared to conventional methods.
- Velmathi, Sivan,Vijayaraghavan, Reena,Amarendar, Ch.,Pal, Ravindra P.,Vinu, Ajayan
-
experimental part
p. 2733 - 2736
(2010/12/25)
-
- One-pot synthesis of amine-substituted aryl sulfides and benzo[ b ]thiophene derivatives
-
A series of amine-substituted aryl sulfides have been synthesized from nitroaryl halides via a simple one-pot procedure involving metal-free C-S cross-coupling and in situ nitro group reduction. Various nitroaryl halides were reacted with thiols in recyclable poly(ethylene glycol) to afford the amine-substituted aryl sulfides in high yield. Additionally, the cross-coupling reactions of nitro- and aldehyde-substituted aryl halides with benzyl thiols under the same reaction conditions were demonstrated to afford benzothiazole and phenylbenzo[b]thiophene derivatives.
- Duan, Zhongyu,Ranjit, Sadananda,Liu, Xiaogang
-
supporting information; experimental part
p. 2430 - 2433
(2010/07/10)
-
- Synthesis and fungicidal activity of bis(2-arylcarbonylamino-1H- benzimidazol-5-yl) sulfones
-
A procedure has been developed for the synthesis of bis(2- arylcarbonylamino-1H-benzimidazol-5-yl) sulfones by reaction of the corresponding substituted benzoyl chloride with sodium cyanamide and subsequent treatment of the N-cyanobenzamide thus formed with 3,3′,4,4′- tetraaminodiphenyl sulfone in acid medium. The products were tested for fungicidal activity.
- Pilyugin,Kuznetsova,Sapozhnikov,Chikisheva,Kiseleva,Vorob'eva,Klimakova,Sapozhnikova,Davletov,Galeeva
-
p. 446 - 450
(2008/09/19)
-
- Thermoplastic resin composition and a method of molding the same
-
This invention provides a thermoplastic resin composition comprising a thermoplastic resin and 0.1 to 100 parts by weight, per 100 parts by weight of the thermoplastic resin, of an imide compound prepared, e.g., by dehydration condensation of 1,2,3,4-butanetetracarboxylic acid or a monoanhydride or a dianhydride thereof with a primary amine, and a method of molding the resin composition.
- -
-
-
- Basic azo dyestuffs of the 3-cyano-2,4,6-triamino pyridine series
-
The new basic azo dyestuffs of the formula STR1 wherein the symbols have the meaning given in the description, are suitable for dyeing synthetic and naturally occurring substrates which can be dyed with basic dyestuffs.
- -
-
-
- Synthesis of phthalonitrile resins containing ether and imide linkages
-
Imide-containing phthalonitrile monomers are prepared from a phthalonitrile and an aromatic dianhydride. The monomer and a method for preparing the monomer is disclosed. These monomers are synthesized into heat resistant polymers and copolymers with aromatic ring structure incorporating imide and ether linkages. The synthesis of the high temperature thermosetting polymers and copolymers is also disclosed.
- -
-
-
- Antiparasitic Agents: Part 5 - Synthesis of 4-(Substituted-aryl)amino-7-chloroquinolines as Potential Antimalarial Agents
-
A series of 4-(4- and 3-substituted-aryl)amino-7-chloroquinolines (11-15, 17, 18, 28) and substituted diphenyl sulphones (8-10, 19-27) have been synthesized and tested for their antiparasitic activity against Plasmodium berghei in mice, Litomosoides carinii in cotton rats and Hymenolepis nana in mice.Of the compounds tested, 11 shows 100percent activity against P. berghei at a dose of 10 mg/kg x 5 days in mice while 23 is effective in eliminating 100percent of the H. nana worms from mice at a single oral dose of 250 mg/kg.
- Chauhan, P. M. S.,Sharma, Satyavan,Bhakuni, D. S.
-
p. 1142 - 1145
(2007/10/02)
-
- Use of Potassium Bromate. Oxidation of Organic Sulphur Compounds
-
Oxidation of various organic sulphur compounds by potassium bromate under different experimental conditions was studied.
- Adak, Mohini Mohan,Banerjee, Gopal Chandra,Banerjee, Amalendu
-
p. 224 - 228
(2007/10/02)
-
- Bis-(maleamic acid) derivatives of triamines
-
The compositions described herein comprise polyimides having bis-maleimide terminal groups and having the formula: STR1 wherein Q is a trivalent aromatic radical, Ar is a divalent aromatic radical, Ar" is a tetravalent aromatic radical and n has a value of 0-20. Derivatives may be made of these compounds by homopolymerization, copolymerization with other copolymerizable materials and by reaction with Diels-Alder reactable materials.
- -
-
-
- Silicone containing bis-thioether aromatic amines
-
A silicone containing bis-thioether aromatic amine has a chemical structure wherein an aromatic nucleus at each end of the chemical radical is chemically bonded to the remainder of the chemical radical by either sulfur, sulfoxide or sulfone.
- -
-
-
