633303-87-4Relevant academic research and scientific papers
Visible-Light-Driven Halogen-Bond-Assisted Direct Synthesis of Heteroaryl Thioethers Using Transition-Metal-Free One-Pot C-I Bond Formation/C-S Cross-Coupling Reaction
Nandy, Anuradha,Kazi, Imran,Guha, Somraj,Sekar, Govindasamy
, p. 2570 - 2581 (2021/02/27)
An efficient protocol for the synthesis of thioether directly from heteroarenes has been developed in the presence of visible light in a one-pot manner at room temperature. This method involves two sequential reactions in a single pot where the formation of the iodinated heteroarene is followed by a transition-metal-free C-S coupling reaction. A wide range of heteroarene and thiol partners (including aliphatic thiols) have been used for the synthesis of thioethers. NMR studies and DFT calculations revealed the presence of a halogen bond between the thiolate anion (halogen bond acceptor) and iodoheteroarene (halogen bond donor). This halogen bonded complex on photoexcitation facilitates the electron transfer from the thiolate anion to the iodoheteroarene at room temperature.
Palladium-Catalyzed Direct C2-Biarylation of Indoles
Murugesan, Tamilarasu,Sivarajan, Chinraj,Jayakumari, Chithra Mohan,Singh, Rajat Kumar,Vennapusa, Sivaranjana Reddy,Kaliyamoorthy, Alagiri
supporting information, p. 10838 - 10851 (2021/08/16)
Biaryl and indole units are important structural motifs in several bioactive molecules and functional materials. We have accomplished straightforward access to C2-biarylated indole derivatives through palladium-catalyzed C-H activation strategy with a bro
Regioselective C-H sulfenylation ofN-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles
Hao, Shuai,Hu, Jingyan,Ji, Xiaoming,Lai, Miao,Ren, Tianbao,Wang, Erbin,Wang, Juanjuan,Wu, Zhiyong,Xi, Gaolei,Zhao, Mingqin
, p. 31819 - 31823 (2020/09/21)
This paper describes the regioselective C-3 sulfenylation ofN-sulfonyl protected 7-azaindoles with sulfonyl chlorides. In this transformation, dual roles of TBAI serving as both promoter and desulfonylation reagent have been demonstrated. The reaction proceeded smoothly under simple conditions to afford 3-thio-7-azaindoles in moderate to good yields with broad substrate scopes. This protocol refrains from using transition-metal catalysts, strong oxidants or bases, and shows its practical synthetic value in organic synthesis.
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.].
Regioselective deoxidation thionation reaction for 7-azaindole-nitrogen oxide
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Paragraph 0028-0034, (2020/02/17)
The invention relates to the fields of organic synthesis and medicine and chemical industry, in particular relates to an iodine-catalyzed regioselective deoxidation thionation reaction method for 7-azaindole-nitrogen oxide, and aims to overcome the proble
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.
Regioselective deoxygenative chalcogenation of 7-Azindole: N-oxides promoted by I2/PEG-200
Liu, Shanshan,Yang, Heng,Jiao, Lin-Yu,Zhang, Jian-Hua,Zhao, Chen,Ma, Yangmin,Yang, Xiufang
supporting information, p. 10073 - 10087 (2019/12/23)
We developed a general and sustainable approach for the regioselective deoxygenative chalcogenation of 7-Azindole N-oxides; the combination of an internal oxidant and a green solvent has been used successfully for the synthesis of mono-and dichalcogenyl 7-Azaindoles which are of pharmaceutical interest. The regioselectivity is tunable by the variation of the reaction conditions. I2/PEG was established as an efficient and reusable catalytic system for C-H chalcogenation. This developed methodology has great potential for practical utility, with a broad substrate scope, green reaction conditions, and operational simplicity.
Alkali-catalyzed green synthesis method of 3-arylthio-7-azaindole compound
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Paragraph 0030-0034, (2019/03/08)
The invention discloses an alkali-catalyzed green synthesis method of a 3-arylthio-7-azaindole compound. The alkali-catalyzed green synthesis method comprises the steps: adding 7-azaindole and an arylthio reagent into a solvent, then, adding a catalyst, a
Iodine-catalysed versatile sulfenylation of indoles with thiophenols: controllable synthesis of mono- and bis-arylthioindoles
Zhang, Hailei,Bao, Xiaoze,Song, Yuming,Qu, Jingping,Wang, Baomin
, p. 8885 - 8891 (2015/11/02)
A versatile method for the synthesis of mono- and bis-arylthioindoles via I2 catalysed direct oxidative sulfenylation of indoles with thiophenols (especially mercaptobenzoic acids) has been presented. This system features environmental friendliness, easy operation, and mild reaction conditions, and shows a broad functional group tolerance furnishing good to excellent yields.
