- Sequential C-H activation enabled expedient delivery of polyfunctional arenes
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Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.
- Cai, Xiaoqing,Chen, Qian,Chen, Xiaojian,Gao, Yang,Huo, Yanping,Li, Xianwei,Ouyang, Wensen,Rao, Jianhang,Wang, Jie
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supporting information
p. 8075 - 8078
(2021/08/20)
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- Ortho-position imine ester or cyano substituted aryl thioether derivative, and preparation method and application thereof
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The invention belongs to the technical field of organic synthesis, and particularly relates to an ortho-position imine ester or cyano substituted aryl thioether derivative, and a preparation method and an application thereof. The structural formula of the ortho-position imine ester or cyano substituted aryl thioether derivative is represented by formula (I) or formula (I'). The preparation methodcomprises the following steps: selecting an imine ester substrate and different substituted disulfide coupling reagents, mixing the reactants with a catalyst, an oxidant and a halide ion capturing agent under air atmosphere and alkaline conditions, and carrying out an aromatic ring ortho-position carbon-hydrogen bond activation reaction to obtain the ortho-position imine ester or cyano substitutedaryl sulfide derivative. The preparation method is simple and easily available in substrate and simple to operate, and achieves the efficient synthesis of the aryl thioether derivative of ortho-position imine ester or cyano group through the regulation of a catalytic system; and the product can be applied to later-stage derivatization reaction of drug molecules such as probenecid, and synthesis potential is provided for rapid construction of thioether derivatives with bioactive molecule libraries.
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Paragraph 0131-0135
(2020/06/17)
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- Facile synthesis of 1,2-thiobenzonitriles: Via Cu-catalyzed denitrogenative radical coupling reaction
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A Cu-catalyzed synthesis of 1,2-thiobenzonitriles via oxidative C-N cleavage of 3-aminoindazoles followed by radical coupling with thiols is developed. A diverse array of 1,2-thiobenzonitriles were obtained in good yields with wide substrate scope. Notably, this is the first example of denitrogenative radical coupling with 3-aminoindazoles.
- Zhou, Yao,Wang, Ya,Lou, Yixian,Song, Qiuling
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supporting information
p. 10265 - 10268
(2019/09/03)
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- Synthesis of Functionalized Diaryl Sulfides by Cobalt-Catalyzed Coupling between Arylzinc Pivalates and Diaryl Disulfides
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An efficient protocol for the cobalt-catalyzed preparation of diaryl sulfides from solid organozinc pivalates and commercially available diaryl disulfides is reported. This cross-coupling proceeds at room temperature and displays a good functional group tolerance, allowing the preparation of a diversity of symmetrical or asymmetrical diaryl sulfides in 60-95% yield.
- Dong, Zhi-Bing,Balkenhohl, Moritz,Tan, Eric,Knochel, Paul
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p. 7581 - 7584
(2018/11/27)
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- A medicine intermediate diaryl sulfide synthetic method of the compound
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The invention relates to a synthetic method for a medical intermediate diaryl sulfide compound. The method comprises: in an organic solvent, in the presence of a catalyst, alkali, a phosphine-containing ligand and an auxiliary, carrying out reaction on a compound shown in the formula (I) and a compound shown in the formula (II) to obtain a compound shown in the formula (III), wherein the formula (III) is shown in the description; R is H, C1-C6 alkyl, C1-C6 alkoxyl or halogen. According to the method provided by the invention, the catalyst, the alkali, the phosphine-containing ligand, the auxiliary and the solvent are properly selected and combined, so that the components play a role of unique synergistic effect each other, and the target product can be obtained with a high yield, thereby providing a brand new method for synthesizing the compounds. The synthetic method has a good application prospect and industrial production potential in the technical field of organic synthesis, particularly the field of medical intermediate synthesis.
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Paragraph 0049; 0050; 0051; 0052
(2017/08/25)
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- Activation of aryl thiocyanates followed by aryne insertion: Access to 1,2-thiobenzonitriles
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Palladium-catalyzed activation of carbon-sulfur bonds allows aryne insertion into aryl thiocyanates to generate new C-SAr and C-CN bonds in one step. The readily available starting materials make this method efficient in generating a variety of 1,2-thiobenzonitriles. By choosing an oxygen atmosphere the yields are increased and side reactions are minimized.
- Pawliczek, Martin,Garve, Lennart K. B.,Werz, Daniel B.
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supporting information
p. 1716 - 1719
(2015/04/14)
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- Iridium and phosphine promoted C-F bond activation: The C-S cross-coupling of aryl fluorides with diaryl disulfides to synthesize thioethers
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Carbon-fluorine bond is the strongest known single bond to carbon and proved very difficult to cleave. An iridium and phosphine promoted C-F bond activation was developed, for the first time achieving the C-S cross-coupling reaction of disulfides with aryl fluorides using iridium complex. The corresponding monoarylthiolation products were obtained at moderate to good yields. Thus, it represents a new method for the synthesis of aryl sulfides through C-F bond activation.
- Li, Liang,Miao, Hongyan,Ding, Yuqiang
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supporting information
p. 6405 - 6408
(2015/11/16)
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- Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides: P-orientation in the polyarylthiolation of polyfluorobenzenes
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In the presence of a catalytic amount of RhH(PPh3)4 and 1,2-bis(diphenylphosphino)benzene, an aromatic fluoride, an organic disulfide (0.5 equiv), and triphenylphosphine (0.5 equiv) reacted in refluxing chlorobenzene to give an aryl sulfide in high yield. Since triphenylphosphine trapped fluoride atoms forming phosphine difluoride, both organothio groups of the disulfide reacted effectively, and the fluoride substituent reacted more readily than the chloride and bromide. The reaction of hexafluorobenzene and a diaryl disulfide gave 1,4-diarylthio-2,3,5,6-tetrafluorobenzene, 1,2,4,5-tetraarylthio-3,6-difluorobenzene, and hexaarylthiobenzene in a stepwise manner; pentafluorobenzene gave 1-arylthio-2,3,5,6-tetrafluorobenzene; 1,2,3,4-tetrafluorobenzene gave 1,2-diarylthio-3,6-difluorobenzene; and 1,2,4,5-tetrafluorobenzene gave 1,4-diarylthio-2-5-difluorobenzene. The polyarylthiolation reaction of polyfluorobenzenes exhibited a strong tendency to form 1,4-difluorobenzenes. Copyright
- Arisawa, Mieko,Suzuki, Takaaki,Ishikawa, Tomofumi,Yamaguchi, Masahiko
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supporting information; scheme or table
p. 12214 - 12215
(2009/02/04)
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- Enantioselective palladium catalysed allylic substitution. Electronic and steric effects of the ligand.
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Ligands containing an enantiomerically pure oxazoline and a sulfur-containing tether have been examined for their ability to provide asymmetric induction in palladium catalysed allylic substitution reaction. The enantioselectivity obtained was found to be
- Allen,Bower,Williams
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p. 1895 - 1898
(2007/10/02)
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- POTENTIAL ANTIDEPRESSANTS: 1-(2-(METHOXY- AND HYDROXY-PHENYLTHIO)PHENYL)-2-PROPYLAMINES
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2-(Methoxyphenylthio)benzaldehydes Xa-Xd were reacted with nitroethane in boiling acetic acid to give the corresponding 1-aryl-2-nitropropenes XIIa-XIId: benzonitriles XIIIa and XIIIc and benzaldoximes XXIc and XXId were isolated as by-products.Chromatogr
- Urban, Jiri,Sedivy, Zdenek,Holubek, Jiri,Svatek, Emil,Ryska, Miroslav,et al.
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p. 1077 - 1098
(2007/10/02)
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