32884-73-4Relevant academic research and scientific papers
Flavin/I2-Catalyzed Aerobic Oxidative C–H Sulfenylation of Aryl-Fused Cyclic Amines
Jiang, Xinpeng,Zhao, Zongchen,Shen, Zhifeng,Chen, Keda,Fang, Liyun,Yu, Chuanming
, p. 3889 - 3895 (2020/06/01)
We report an aerobic oxidative C–H sulfenylation of aryl-fused cyclic amines with various thiols catalyzed by flavin/I2 for the first time. While flavin I catalyzed the C–H sulfenylation of indolines to afford 3-sulfenylindoles, flavin II enabl
Recyclable Cellulose-Derived Fe3O4@Pd NPs for Highly Selective C–S Formation by Heterogeneously C–H Sulfenylation of Indoles
Li, Shengyi,Wang, Jinguo,Jin, Jianzhong,Tong, Jianying,Shen, Chao
, p. 2409 - 2414 (2020/02/25)
Abstract: An efficient and convenient method was developed for the preparation of 3-sulfenylindoles via a cellulose-derived Fe3O4@Pd NPs catalyzed heterogeneously C–H sulfenylation of indoles. This approach provides an effective synthetic route to an important class of indoles derivatives and features high efficiency, easy operation, good practicality, and environmental friendliness. The recoverable catalyst was separated from the reaction mixture using an outside magnetic field and can be recycled five times without huge loss of catalytic performance. Graphic Abstract: An efficient method was developed for the preparation of 3-sulfenylindoles via cellulose-derived Fe3O4@Pd NPs catalyzed heterogeneously C–H sulfenylation of indoles.[Figure not available: see fulltext.].
Cuprous complex, preparation method thereof and application of cuprous complex in synthesis of 3-indolyl thioether
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Paragraph 0050-0060; 0061, (2020/08/02)
The invention relates to a cuprous complex, a preparation method thereof and an application of the cuprous complex in synthesis of 3-indolyl thioether. The structural formula of the cuprous complex isshown in the specification, Ar is aryl containing a benzene ring or heterocyclic aryl, and ''.'' is a boron hydrogen bond; the preparation method comprises the following steps: 1) dissolving ortho-carborane diformaldehyde and arylamine in an organic solvent, reacting at 60-100 DEG C, and cooling to room temperature after the reaction is finished; and 2) adding CuI, reacting at room temperature for 3-6 hours, and separating to obtain the cuprous complex. Compared with the prior art, the cuprous complex containing the ortho-position carborane Schiff base ligand can efficiently catalyze the coupling reaction of synthesizing a 3-indolyl thioether compound from indole and thiophenol, the method has the advantages of high selectivity, low catalyst dosage, mild reaction conditions, open reaction(taking air as an oxidant), high reaction rate, high yield, wide substrate range and the like and shows a wide industrial application prospect.
Domino C?S/C?N Bond Formation Using Well-Defined Copper-Phosphine Complex Catalyst: Divergent Approach to 3-Sulfenylated Indoles
Tamargo, Ramuel John Inductivo,Kim, Sung Hong,Lee, Yong Rok
, p. 4005 - 4015 (2019/07/18)
A protocol was developed for the synthesis of 3-thioindoles in good-to-excellent yields involving sulfenylation between 2-nitrocinnamaldehydes and various thiols using a well-defined copper(I)-phosphine complex catalyst. This unconventional divergent approach involves in situ generation of indoles via domino C?S/C?N bond formation initiated by sulfa-Michael addition followed by intramolecular N-heteroannulation. This protocol shows good chemoselectivity and broad substrate scope. To briefly demonstrate the value of this approach, 2-benzoyl-3-sulfenylated indoles were prepared from commercially available 2-nitrochalcones and thiols. (Figure presented.).
NH4I/1,10-phenanthroline catalyzed direct sulfenylation of N-heteroarenes with ethyl arylsulfinates
Chen, Lingjuan,Zhang, Jun,Wei, Yueting,Yang, Zhen,Liu, Ping,Zhang, Jie,Dai, Bin
, (2019/10/14)
An efficient synthesis of N-heterocyclic aryl sulfides via NH4I/1,10-phenanthroline-catalyzed direct sulfenylation reactions was reported. In this reaction, heteroarenes such as indoles, and pyrroles serve as nucleophiles by installing a arylthio group at the C3 and C2 position of heterocycles, respectively. With readily accessible and free of unpleasant odor ethyl arylsulfinates as sulfur reagents, the metal-free-catalyzed direct sulfenylation of N-heteroarenes has been developed. 3-Arylthio-indoles and 2-arylthio-pyrroles derivatives were obtained in moderate to excellent yields, even on gram scale. The reaction was general for a broad scope of substrates and demonstrated good tolerance to a variety of functional groups.
Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot
Equbal, Danish,Singh, Richa,Saima,Lavekar, Aditya G.,Sinha, Arun K.
, p. 2660 - 2675 (2019/03/14)
Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge.
Synergistic Cooperative Effect of Sodium borohydride-Iodine Towards Cascade C?N and C?S/Se Bond Formation: One-pot Regioselective Synthesis of 3-Sulfenyl/selenyl Indoles and Mechanistic Insight
Lavekar, Aditya G.,Equbal, Danish,Saima,Sinha, Arun K.
, p. 180 - 185 (2018/01/12)
In this work, a new strategy to synthesize 3-sulfenyl/selenyl indole is reported wherein LC?MS reveals a novel insight into synergistic cooperative effect of NaBH4-I2 which allows cascade C?N and C?S/C?Se bond formations via reduction-nucleophilic cyclization-chalcogenylation, three steps in one-pot, towards regioselective synthesis of diverse 3-chalcogenyl indoles including 5-bromo-3-[(3,4,5-trimethoxyphenyl)thio]-1H-indole, a known lead anticancer compound, directly from 2-amino-phenacylchlorides and thiophenols or disulfides/diselenides in aqueous dioxane under transition-metal-free condition. (Figure presented.).
Synthesis of 3-Sulfenylindoles from Indoles and Various Sulfenylation Agents through Aerobic Oxidative C-S Bond Coupling
Xu, Chaorong,Yi, Shanli,Li, Meichao,Hu, Xinquan,Sun, Nan,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu
supporting information, p. 1914 - 1920 (2018/08/28)
A novel aerobic catalytic oxidation system for the sulfenylation of indoles with a variety of sulfenylation agents through oxidative C-S bond coupling has been successfully developed. The reactions were performed with potassium iodide as the catalyst, sodium nitrite as the co-catalyst, and molecular oxygen as the terminal oxidant in the presence of acetic acid. Under the optimal reaction conditions, a number of indoles could be sulfenylated with Bunte salts, thiols, or disulfides to generate 3-sulfenylindoles in good yields. This protocol provided an efficient and environmentally benign strategy for the synthesis of 3-sulfenylindoles.
3 - Mercapto of indole compounds synthesized by catalytic oxidation method (by machine translation)
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Paragraph 0086; 0087, (2018/10/11)
The invention discloses a 3 - mercapto of indole compounds synthesized by catalytic oxidation method, to indole compounds and sulfur on behalf of the sulfate as the substrate of reaction, to potassium iodide and sodium nitrite as catalyst, in order to acetic acid as an auxiliary agent, in order to oxygen as the oxidizing agent, the reaction substrate in the organic solvent, for normal pressure, temperature 50 - 80 °C reaction under the condition of, after the reaction is completed after the separation and processed to obtain the 3 - mercapto-indole compounds. The synthesizing method of the invention, simple and safe operation, in order to clean the oxygen as terminal oxidant, thereby greatly reducing the environmental costs; mild reaction conditions. (by machine translation)
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.
