- Visible light-induced mono-bromination of arenes with BrCCl3
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A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.
- Fan, Jiali,Wei, Qiancheng,Zhu, Ershu,Gao, Jing,Cheng, Xiamin,Lu, Yongna,Loh, Teck-Peng
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supporting information
p. 5977 - 5980
(2021/06/18)
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- Hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups, preparation method and applications thereof
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The invention discloses a hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups, a preparation method and applications thereof.According to the invention, the hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups is obtained through a Stille coupling reaction and a metal coordination reaction; the metal organic small molecule cooperation compound belongs to branched small molecules, the structure of the metal organic small molecule cooperation compound uses a metal as a core, and a branched chain contains hydroxyquinoline and a perylene diimide and electron-donating aromatic group unit; hydroxyquinoline has high electron withdrawing capacity, the grafted perylene diimide unit is beneficial to improving the crystallization capacity and the electron affinity of small molecules, the electron donating capacity is enhanced by linking the electrondonating aromatic group to the perylene diimide unit, and the push-pull electron effect is easily formed with the hydroxyquinoline; and the structure small molecule and the polymer donor form energylevel matching, so that the structure small molecule is suitable for being used as a small molecule acceptor material.
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Paragraph 0030-0033
(2020/03/06)
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- Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes
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Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.
- Jianbo, He,Tingting, Zhou,Yongjing, Cao,Yuanyuan, Zhang,Weiqing, Yang,Menglin, Ma
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p. 1121 - 1126
(2018/08/17)
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- A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines
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An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.
- Motati, Damoder Reddy,Uredi, Dilipkumar,Watkins, E. Blake
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p. 1782 - 1788
(2018/02/23)
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- Chemo-and regioselective bromination of aromatic compounds in the presence of γ-picolinium bromochromate (γ-PBC)/CH3CN
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Regioselective oxidative bromination of activated aromatic compounds has been studied using γ-Picolinium bromochromate in either CH3COOH or CH3CN is reported. The results obtained revealed excellent yields of monobromo compounds at para-position under thermal condition especially in methyl cyanide.
- Mahmoodi,Yazdanbakhsh,Hassanzadeh
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experimental part
p. 429 - 434
(2012/04/04)
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- Mild, efficient, and regioselective monobromination of arylamines and phenols using [BBIm]Br3 as a new reagent
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We report here an efficient method for the synthesis and characterization of the room-temperature ionic liquid 1,3-di-n-butylimidazolium tribromide ([BBIm]Br3) (2) and its application as an efficient reagent and solvent for regioselective bromination of arylamines and phenols under mild conditions. The bromination was carried out in the absence of organic solvents, and in most cases, the only extraction solvent needed was water. The spent 1,3-di-n-butylimidazolium bromide (1) was easily recycled.
- Borikar, Sanjay P.,Daniel, Thomas,Paul, Vincent
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experimental part
p. 647 - 653
(2011/02/27)
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- A new method of bromination of aromatic rings by an iso-amyl nitrite/HBr system
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A mixture of iso-amyl nitrite/HBr is shown to be a mild and efficient reagent for electrophilic aromatic bromination. The reaction succeeds with slightly activated arenes and heterocyclic compounds. By using HCl instead of HBr, chlorination can also be performed in few cases. The i-amONO2/HBr mixture can also be utilized for bromination in the α-position of electron withdrawing groups. A possible mechanism is briefly discussed.
- Gavara, Laurent,Boisse, Thomas,Rigo, Beno?t,Hénichart, Jean-Pierre
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p. 4999 - 5004
(2008/09/21)
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