124589-41-9Relevant articles and documents
Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information, (2021/01/04)
N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.
Synthesis of 3-halogenated 2,3′-biindoles by a copper-mediated 2,3-difunctionalization of indoles
Gu, Xiaoting,Liang, Taoyuan,Wei, Wanxing,Zhang, Xiaoxiang,Zhang, Yingying,Zhang, Zhuan
supporting information, p. 10403 - 10407 (2021/12/17)
A copper-mediated 2,3-difunctionalization of indoles to afford 3-halogenated 2,3′-biindoles is described herein. The protocol uses readily available feedstocks and a naturally abundant copper catalyst system, which allows the regioselective formation of C-C and C-X (X = Cl & Br) bonds in one single operation. Here the copper metal salt serves not only as a catalyst but also as a reactant to provide the source of halogen. This operationally simple procedure avoids the utilization of environmentally unfriendly reagents and displays good functional group compatibility. Noteworthily, the introduction of halogen into molecules would offer great potential for further chemical transformations. This journal is
Sulfoxide-Promoted Chlorination of Indoles and Electron-Rich Arenes with Chlorine as Nucleophile
Ji, Yuan-Zhao,Li, Hui-Jing,Wang, Yi-Ruo,Wu, Yan-Chao,Zhang, Zheng-Yan
supporting information, (2020/02/05)
An efficient chlorination of indoles and electron-rich arenes with chlorine anion as nucleophile is described. With the use of ethyl phenyl sulfoxide as the promoter, the reaction went smoothly under metal-free and mild conditions. Various indoles and electron-rich arenes are converted into the corresponding chlorinated compounds in moderate to excellent yields. A plausible interrupted Pummerer reaction mechanism was proposed without the oxidation of chloride anion. In addition, the byproduct thioether could be easily converted to the starting material sulfoxide just by a simple oxidation reaction. (Figure presented.).
Atroposelective Haloamidation of Indoles with Amino Acid Derivatives and Hypohalides
Li, Zhaojie,Tang, Menghan,Hu, Chenyang,Yu, Shouyun
supporting information, p. 8819 - 8823 (2019/11/11)
An atroposelective coupling of indoles with chiral amino acid-based sulfonamides mediated by hypohalides is described. A series of 2-amido-3-haloindoles with a C-N chiral axis are delivered using this strategy. The C3 halogen atoms can facilitate further
Controllable synthesis of 3-chloro- and 3,3-dichloro-2-oxindoles via hypervalent iodine-mediated chlorooxidation
Jiang, Xinpeng,Yang, Liechao,Yang, Wenlong,Zhu, Yu,Fang, Liyun,Yu, Chuanming
supporting information, p. 6920 - 6924 (2019/07/22)
An efficient and controllable protocol for the synthesis of 3-chloro- and 3,3-dichloro-2-oxindoles has been developed via hypervalent iodine-promoted chlorooxidation. By using two equivalents of 1-chloro-1,2-benziodoxol-3-(1H)-one, a wide range of indoles
Visible-Light-Induced Direct Oxidative C?H Amidation of Heteroarenes with Sulfonamides
Tong, Kun,Liu, Xiaodong,Zhang, Yan,Yu, Shouyun
supporting information, p. 15669 - 15673 (2016/10/25)
A direct oxidative C?H amidation of heteroarenes with sulfonamides via nitrogen-centered radicals has been achieved. Nitrogen-centered radicals are directly generated from oxidative cleavage of N?H bonds under visible-light photoredox catalysis. Sulfonami
Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin
Yan, Jianwei,Ni, Tianjun,Yan, Fulin
supporting information, p. 1096 - 1098 (2015/02/19)
Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions.
A practical lewis base catalyzed electrophilic chlorination of arenes and heterocycles
Maddox, Sean M.,Nalbandian, Christopher J.,Smith, Davis E.,Gustafson, Jeffrey L.
supporting information, p. 1042 - 1045 (2015/03/30)
A mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodology is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable, underscoring the mild nature of this chemistry. Lewis base catalysis was also found to improve several diverse aromatic brominations and iodinations.
2,4,6-Tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine as a new recyclable hypervalent iodine(III) reagent for chlorination and oxidation reactions
Thorat, Prerana B.,Bhong, Bhagyashree Y.,Karade, Nandkishor Y.
supporting information, p. 2061 - 2066 (2013/10/21)
The synthesis of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine, as a new recyclable nonpolymeric analogue of (dichloroiodo)benzene, is achieved in two steps using 2,4,6-trichloro-1,3,5-triazine and 4-iodophenol. The application of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine for the chlorination reaction of various activated arenes, olefin, and 1,3-diketone is demonstrated. The reagent 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine can be applied also for the oxidative synthesis of 1,3,4-oxadiazoles and 1,2,4-thiadiazoles under mild conditions in excellent yields. The recyclability of the 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine was possible owing to the facile recovery and reuse of the coproduced 2,4,6-tris(4-iodophenoxy)-1,3,5- triazine from the reaction mixture due to its practical insolubility in methanol. Georg Thieme Verlag Stuttgart, New York.
Pd(II)-catalyzed bromo- and chlorodecarboxylation of electron-rich arenecarboxylic acids
Peng, Xuefeng,Shao, Xiang-Feng,Liu, Zhong-Quan
supporting information, p. 3079 - 3081 (2013/07/11)
A bromo- and chlorodecarboxylation of various aromatic carboxylic acids catalyzed by Pd(II) has been developed in this work. A series of electron-rich arenecarboxylic acids gave the corresponding decarboxylative monohalogenation products under the typical reaction conditions.
