14453-85-1Relevant academic research and scientific papers
Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides
Pan, Lei,Cooke, Maria Victoria,Spencer, Amara,Laulhé, Sébastien
, p. 420 - 425 (2021/11/01)
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.
Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2
Wang, Rongkang,Chen, Fangming,Jiang, Lvqi,Yi, Wenbin
supporting information, p. 1904 - 1911 (2021/02/12)
An efficient electrochemical synthesis approach of various unsymmetrical thioethers and arylboronates has been developed. Bench stable arylazo sulfones were used as radical precursors for carbon-heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and even added bases, but also exhibited favorable functional group tolerance. (Figure presented.).
Flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines
Jiang, Xinpeng,Shen, Zhifeng,Zheng, Cong,Fang, Liyun,Chen, Keda,Yu, Chuanming
supporting information, (2020/07/24)
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.
Method for synthesis of diaryl thioether compound without transition metal catalysis
-
Paragraph 0034-0036, (2019/11/28)
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.
HETEROCYCLIC CARBOXYLIC ACID AMIDE LIGAND AND APPLICATIONS THEREOF IN COPPER CATALYZED COUPLING REACTION OF ARYL HALOGENO SUBSTITUTE
-
Paragraph 0287-0288, (2019/05/15)
Provided are a heterocyclic carboxylic acid amide ligand and applications thereof in a copper catalyzed coupling reaction. Specifically, provided are uses of a compound represented by formula (I), definitions of radical groups being described in the specifications. The compound represented by formula (I) can be used as the ligand in the copper catalyzed coupling reaction of the aryl halogeno substitute, and is used or catalyzing the coupling reaction for forming the aryl halogeno substitute having C—N, C—O, C—S and other bonds.
Crystallographic and SAR analyses reveal the high requirements needed to selectively and potently inhibit SIRT2 deacetylase and decanoylase
Yang, Ling-Ling,Xu, Wei,Yan, Jie,Su, Hui-Lin,Yuan, Chen,Li, Chao,Zhang, Xing,Yu, Zhu-Jun,Yan, Yu-Hang,Yu, Yamei,Chen, Qiang,Wang, Zhouyu,Li, Lin,Qian, Shan,Li, Guo-Bo
supporting information, p. 164 - 168 (2019/01/30)
A high-quality X-ray crystal structure reveals the mechanism of compound 1a inhibiting SIRT2 deacetylase and decanoylase. Structure-activity relationship (SAR) analysis of the synthesized derivatives of 1a reveals the high requirements needed for selectiv
Metal-Free Iodine-Catalyzed Direct Arylthiation of Substituted Anilines with Thiols
Yang, Daoshan,Yan, Kelu,Wei, Wei,Zhao, Jing,Zhang, Mengqi,Sheng, Xuguang,Li, Guoqing,Lu, Shenglei,Wang, Hua
, p. 6083 - 6092 (2015/06/30)
Iodine-catalyzed direct arylthiation of substituted anilines for the synthesis of various diaryl sulfides has been developed under metal- and solvent-free conditions. The present method uses readily available thiols as the arylthiation reagents, and envir
Design, synthesis and antitumor activity of novel cis-furoquinoline derivatives
Li, Jie,Pei, Shuchen,Zhu, Yingxi,Wu, Jianbo,Chen, Yin,Zhang, Weiyu,Wu, Yong
experimental part, p. 379 - 388 (2012/07/03)
A series of novel cis-furoquinoline derivatives was synthesized and tested for their antitumor activities in vitro against HepG2 cells, Lu-04 cells and Leu02 cells to evaluate structure-activity relationships. Assay-based antiproliferative activity study revealed that several compounds had significant effects on cytotoxicity, among which compounds 2f, 2l, 2q were found to be the most active compounds. Above all, compounds 2f, 2l, 2q would be potential anticancer agents which deserved further research.
Microwave-assisted Ullmann-Buchwald C-S bond formation using a copper(I) catalyst and trans-cyclohexane-1,2-diol as ligand
Bagley, Mark C.,Fusillo, Vincenzo,Hills, Edward G.B.,Mulholland, Alex T.,Newcombe, Joseph,Pentecost, Leanne J.,Radley, Emily L.,Stephens, Bethan R.,Turrell, Christopher C.
, p. 294 - 313 (2013/01/16)
Microwave irradiation of a thiophenol or alkyl thiol (1 equiv.) and an aryl halide (1 equiv.) in 2-propanol at 120°C for three hours in the presence of K2CO3 (2 equiv.) as base using copper(I) iodide as catalyst (5 mol%) and trans-cyclohexane-1,2-diol (2 equiv.) as ligand provides a rapid and convenient method for C-S bond formation. The process is most efficient using thiophenol and aryl iodide precursors, both of which may contain electron-donating and electronwithdrawing groups, to give the corresponding diaryl sulfide in good to excellent yield. ARKAT-USA, Inc.
Ligand-free palladium-catalyzed C-S coupling reactions using water as solvent and microwaves
Velmathi, Sivan,Vijayaraghavan, Reena,Amarendar, Ch.,Pal, Ravindra P.,Vinu, Ajayan
experimental part, p. 2733 - 2736 (2010/12/25)
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.
