82946-84-7Relevant articles and documents
Palladium-catalyzed three-component cascade arylthiolation with aryldiazonium salts asS-arylation sources
Li, Jianxiao,Tang, Hao,Lin, Zidong,Yang, Shaorong,Wu, Wanqing,Jiang, Huanfeng
, p. 4071 - 4078 (2020/06/09)
A novel and efficient palladium-catalyzed three-component cascade cyclization/arylthiolation has been developed for the assembly of diverse 3-sulfenylindole and 3-sulfenylbenzofuran derivatives from 2-alkynylamines and 2-alkynylphenols, aryldiazonium salts, and Na2S2O3under aerobic conditions with PEG-200 as an environmentally benign medium. The current study features exceptional functional group tolerance without additional ligands, oxidants or silver salts, and eco-friendly mild reaction conditions. The ionic liquid [C2OHmim]Cl plays a crucial role in this protocol as an environmentally friendly additive. Notably, this procedure represents the first example of the use of aryldiazonium salts as directS-arylation sources in this type of chemical transformation.
An electrochemical synthesized by catalytic oxidation of 3 - mercapto indole compounds
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Paragraph 0103-0104, (2019/05/16)
The invention discloses a synthesizing method for a 3-mercapto indole compound through electrochemical catalytic oxidation. According to the method, a three-electrode system is used, a cathode and ananode are graphite electrodes, and a silver nitrate acetonitrile solution of 0.1mol/L is used as a reference electrode; and the indole compounds, disulfide and potassium iodide are added in a sodium tetrafluoroborate acetonitrile solution, stirring and electrolytic reaction are conducted for 3-24h under the condition of the temperature of 45-75 DEG C and 0.2-0.6 V constant voltage, a reaction solution is post-processed, and the product 3-mercapto indole compound is obtained. By means of the synthesizing method, operation is simple, convenient and safe, the yield of the product 3-mercapto indole compound is high, the reaction condition is mild, clean electrical energy is used as a redox agent, and the environmental cost is greatly reduced.
Direct, Metal-free C(sp2)?H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3
Rafique, Jamal,Saba, Sumbal,Franco, Marcelo S.,Bettanin, Luana,Schneider, Alex R.,Silva, Lais T.,Braga, Antonio L.
supporting information, p. 4173 - 4180 (2018/02/06)
Herein, we report a greener protocol for the synthesis of 3-Se/S-indoles and imidazo[1,2-a]pyridines through direct C(sp2)?H bond chalcogenation of heteroarenes with half molar equivalents of different dichalcogenides, using KIO3 as a non-toxic, easy-to-handle catalyst and a stoichiometric amount of glycerol. The reaction features are high yields, based on atom economy, easy performance on gram-scale, metal- and solvent-free conditions as well as applicability to different types of N-heteroarenes.
Electrochemical sulfenylation of indoles with disulfides mediated by potassium iodide
Chen, Chen,Niu, Pengfei,Shen, Zhenlu,Li, Meichao
, p. G67 - G74 (2018/05/22)
A novel electrochemical system for sulfenylation of indoles with disulfides to generate 3-sulfenylindoles via C-S bond formation mediated by potassium iodide at a low potential was developed. Iodine was electrogenerated from iodide ions at a graphite anode and showed a high catalytic activity for the electrochemical sulfenylation reactions. A variety of aromatic, heteroaromatic and aliphatic disulfides could react with 2-methlyindole to synthesize the corresponding 3-sulfenylindoles in good to excellent yields. In addition, protected and unprotected indoles with various groups, especially electron-donating groups, also performed well in the sulfenylation reactions. The transformation, which proceeded through the redox of iodine and the generation of intermediate 3-iodoindole, provided an efficient and environmentally benign protocol for the synthesis of 3-sulfenylindoles under mild conditions.
NH4I-catalyzed chalcogen(S/Se)-functionalization of 5-membered N-heteroaryls under metal-free conditions
Bettanin, Luana,Saba, Sumbal,Doerner, Carlos V.,Franco, Marcelo S.,Godoi, Marcelo,Rafique, Jamal,Braga, Antonio L.
, p. 3971 - 3980 (2018/06/12)
Herein, we described the NH4I-catalyzed C–H bond chalcogenation of N-heteroaryls in the presence of a minimum amount of DMSO/H2O/acetic acid as additives (2.5/2.5/1 M equiv., respectively), under metal-free conditions. Under optimized conditions, a wide variety of sulfenyl/selenyl imidazo[1,2-α]pyridines were prepared in very good yields. Moreover, the present approach was also highly efficient for the chalcogenation of different 5-membered N-heteroaryls, e.g., indole, imidazothiazole, indazole and imidazopyrimidine derivatives.
Visible-light promoted synthesis of 3-arylthioindoles from indoles and diaryl disulfides
Ye, Lin-miao,Chen, Jie,Mao, Peng,Zhang, Xue-jing,Yan, Ming
supporting information, p. 2743 - 2746 (2017/06/23)
3-Arylthioindoles could be synthesized in good yields via the photoirradiation of indoles and disulfides. The reaction is efficiently promoted by the catalytic amount of sodium iodide. A reaction mechanism involving the electrophilic substitution of indol
Palladium-Catalyzed Oxidative Sulfenylation of Indoles and Related Electron-Rich Heteroarenes with Aryl Boronic Acids and Elemental Sulfur
Li, Jianxiao,Li, Chunsheng,Yang, Shaorong,An, Yanni,Wu, Wanqing,Jiang, Huanfeng
, p. 7771 - 7783 (2016/09/12)
An efficient and convenient palladium-catalyzed C-H bond oxidative sulfenylation of indoles and related electron-rich heteroarenes with aryl boronic acids and elemental sulfur has been described. This procedure provides a useful and direct approach for the assembly of a wide range of structurally diverse 3-sulfenylheteroarenes with moderate to excellent yields from simple and readily available starting materials. Moreover, this synthetic protocol is suitable for N-protected and unprotected indoles. Notably, the construction of two C-S bonds in one step was also achieved in this transformation.
Indium chloride: A versatile Lewis acid catalyst for the synthesis of 3-sulfenylindoles
Praveen Kumar,Dathu Reddy,Venkata Ramana Reddy,Rama Devi,Dubey
, p. 356 - 361 (2014/06/10)
Indium chloride has been used as a versatile Lewis acid catalyst for the synthesis of 3-sulfenylindoles in good yields by the independent reaction of indoles and N-alkylindoles with N-(phenylthio)phthalimide in dimethyl formamide (DMF) at 100°C for about 5-6 h.
Metal-free synthesis of 3-sulfenylindoles via an iodine-mediated electrophilic cyclisation of 2-alkynylanilines with disulfides
Tao, Li-Ming,Liu, Wen-Qi,Zhou, Yun,Li, Ai-Tao
, p. 644 - 646 (2013/02/22)
An efficient and metal-free method was developed to synthesise 3-sulfenylindoles via the iodine-mediated electrophilic cyclisation of 2-alkynylanilines with disulfides. In the presence of I2, various 3-sulfenylindoles were obtained in moderate
Iron-facilitated iodine-mediated electrophilic annulation of N,N-dimethyl-2-alkynylanilines with disulfides or diselenides
Du, Hui-Ai,Tang, Ri-Yuan,Deng, Chen-Liang,Liu, Yan,Li, Jin-Heng,Zhang, Xing-Guo
scheme or table, p. 2739 - 2748 (2011/12/01)
An efficient synthesis of N-methyl-3-chalcogeno-indoles has been developed via iodine-mediated electrophilic annulation reactions of 2-alkynylaniline derivatives with disulfides or diselenides. In the presence of iodine and iron, a variety of 2-alkynylani
