29289-16-5Relevant academic research and scientific papers
Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate
Hussain, Anwar,Sarkar, Akash Mamon,Sereda, Grigoriy,Zefirov, Nikolai
, p. 1140 - 1146 (2020/04/01)
Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N -acetyl- p -toluidine, electrophilic iodination is accompanied by a small extent of chlorination.
Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
, (2019/06/13)
Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
, p. 7411 - 7417 (2019/06/18)
Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp2 C–H bond activation in ball mills
Liu, Zi,Xu, Hui,Wang, Guan-Wu
supporting information, p. 430 - 435 (2018/02/27)
A solvent-free palladium-catalyzed ortho-iodination of acetanilides using N-iodosuccinimide as the iodine source has been developed under ball-milling conditions. This present method avoids the use of hazardous organic solvents, high reaction temperature,
Cobalt(II)-catalyzed regioselective C-H halogenation of anilides
Li, Ze-lin,Sun, Kang-kang,Cai, Chun
supporting information, p. 5433 - 5440 (2018/08/12)
A cobalt-catalyzed regioselective C-H halogenation methodology is reported herein. The highlight of this work is the highly selective C-H functionalization of anilides, which results in high-yielding, versatile, and practical halogenated products. Thereby, brominations, chlorinations and iodinations of many electron-rich and electron-deficient anilides were achieved in a highly selective fashion. Mechanistic studies with respect to the pathway of the reaction are also described.
PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles
Chaisan, Nattawadee,Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
supporting information, p. 675 - 680 (2018/01/18)
An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.
Highly Chemo- and Stereoselective Catalyst-Controlled Allylic C?H Insertion and Cyclopropanation Using Donor/Donor Carbenes
Zhu, Dong,Chen, Lianfen,Zhang, He,Ma, Zhiqiang,Jiang, Huanfeng,Zhu, Shifa
supporting information, p. 12405 - 12409 (2018/09/18)
The highly chemo-, enantio-, and diastereoselective catalyst-controlled intramolecular allylic C?H insertion and cyclopropanation of donor/donor carbenes are reported. The RuII/Pybox complex selectively catalyzed the intramolecular allylic C?H
Monoprotected l-Amino Acid (l-MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)?H Bonds by Iridium(III) Catalysis
Kathiravan, Subban,Nicholls, Ian A.
, p. 7031 - 7036 (2017/05/29)
Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected l-amino acid (l-MPAA) accelerated iridium(III)-catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l-MPAA-catalyzed general halogenation of (hetero)arenes through C(sp2)?H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative.
Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation
Shen, Hongjuan,Fu, Junkai,Yuan, Hao,Gong, Jianxian,Yang, Zhen
, p. 10180 - 10192 (2016/11/17)
A highly effective and straightforward method to construct a wide range of functionalized 2,3-disubstituted indoles has been developed. The method involves the tandem reaction of rhodium(II)-catalyzed denitrogenative annulation of triazole-based benzyl an
Palladium-catalyzed cyclization of 2-alkynyl-N-ethanoyl anilines to indoles: Synthesis, structural, spectroscopic, and mechanistic study
Hoque, Mohammad Mazharol,Halim, Mohammad A.,Sarwar, Mohammed G.,Khan, Md. Wahab
, p. 732 - 742 (2015/11/09)
This study reports a facial regio-selective synthesis of 2-alkyl-N-ethanoyl indoles from substituted-N-ethanoyl anilines employing palladium (II) chloride, which acts as a cyclization catalyst. The mechanistic trait of palladium-based cyclization is also explored by employing density functional theory. In a two-step mechanism, the palladium, which attaches to the ethylene carbons, promotes the proton transfer and cyclization. The gas-phase barrier height of the first transition state is 37kcal/mol, indicating the rate-determining step of this reaction. Incorporating acetonitrile through the solvation model on density solvation model reduces the barrier height to 31kcal/mol. In the presence of solvent, the electron-releasing (-CH3) group has a greater influence on the reduction of the barrier height compared with the electron-withdrawing group (-Cl). These results further confirm that solvent plays an important role on palladium-catalyzed proton transfer and cyclization. For unveiling structural, spectroscopic, and photophysical properties, experimental and computational studies are also performed. Thermodynamic analysis discloses that these reactions are exothermic. The highest occupied molecular orbital-lowest unoccupied molecular orbital gap (4.9-5.0eV) confirms that these compounds are more chemically reactive than indole. The calculated UV-Vis spectra by time-dependent density functional theory exhibit strong peaks at 290, 246, and 232nm, in good agreement with the experimental results. Moreover, experimental and computed 1H and 13C NMR chemical shifts of the indole derivatives are well correlated.
