- Catalyst and Additive-Free Direct Amidation/Halogenation of Tertiary Arylamines with N-haloimide/amides
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An approach has been developed for the amidation (halogenation) of tertiary arylamines by electrophilic activation using N-haloimide/amides. Several control experiments have been performed, and the coupling reaction outcomes indicated that the N-haloimide/amide brings three major functions, including electrophilic activation, aromatic halogenation and nucleophilic nitrogen sources. This cascade reaction features simple manipulation, requires no additional catalyst, oxidant or additives, and is performed under mild conditions. (Figure presented.).
- Xu, Xiu-Juan,Amuti, Adila,Wusiman, Abudureheman
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supporting information
p. 5002 - 5008
(2020/10/06)
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- Selective bromination of pyrrole derivatives, carbazole and aromatic amines with DMSO/HBr under mild conditions
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Bromination of pyrrole derivatives, carbazole and aromatic amines using the DMSO/HBr system affords high yields of the corresponding bromo compounds. Temperature control used in the bromination of anilines helped to promote selective formation of mono- or di-brominated products. Simple operation, low toxicity and high selectivity make this a promising new procedure for the bromination of aromatic compounds.
- Liu, Cong,Dai, Rongji,Yao, Guowei,Deng, Yulin
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p. 593 - 596
(2015/01/09)
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- Electrophilic bromination of alkenes, alkynes, and aromatic amines with iodic acid/potassium bromide under mild conditions
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Bromination of alkenes, alkynes, and aromatic amines has efficiently been carried out at room temperature in short reaction times using HIO 3/KBr in CH2Cl2/H2O (1:1) to prepare corresponding brominated compounds in excellent yields.
- Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Kolvari, Eskandar,Koukabi, Nadiya,Soltani, Hamid,Bayani, Leyla Sharaf
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experimental part
p. 2954 - 2962
(2010/10/20)
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- Elctrophilic bromination of alkenes, alkynes, and aromatic amines with potassium bromide/orthoperiodic acid under mild conditions
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Bromination of alkenes, alkynes, and aromatic amines has efficiently been carried out at room temperature in short reaction times using potassium bromide/orthoperiodic acid in dichloromethane-water (1:1) to prepare the corresponding bromo compounds with excellent yields.
- Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Kolvari, Eskandar,Koukabi, Nadiya,Soltani, Hamid,Komaki, Fatemeh
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experimental part
p. 3672 - 3676
(2010/04/05)
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- {[K.18-Crown-6]Br3}n: a unique tribromide-type and columnar nanotube-like structure for the oxidative coupling of thiols and bromination of some aromatic compounds
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Reaction of 18-crown-6 with KBr and then with bromine (Br2) afforded a unique tribromide salt with a nanotube-like structure ({[K.18-crown-6]Br3}n). Oxidative coupling of thiols and bromination of some aromatic compounds is the first report on the chemistry of this reagent.
- Zolfigol, Mohammad Ali,Chehardoli, Gholamabbas,Salehzadeh, Sadegh,Adams, Harry,Ward, Michael D.
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p. 7969 - 7973
(2008/03/14)
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- Carbanionically Induced -Migrations of ?- and Coordinatively Unsaturated Groups
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According to a general reaction scheme, o-lithioaryl esters 4a,b, amides 13a,b 17b, and amidines 39b of non-enolizable carboxylic acids as well as a corresponding diphenylphosphinic amide 51b react under mild conditions to give the intensely coloured lithium derivatives of o-acylphenoles 6a,b and o-acylarenamines 15a,b, 18a, 41a, 52a, which are finally hydrolyzed to the neutral products 7a,b, 14a,b, 18b, 41b, 52b, respectively.The lithiated precursors of the rearrangement are mostly prepared by halogen/metal exchange reactions.In the case of N,N-di-p-tolylpivalamide 33 such a -rearrangement also could be induced by direct metalation of the educt.With N-methyl-N-phenylpivalamide (29), however, exclusive metalation of the N-methyl group occurs, followed by -migration of the pivaloyl group.Silyl groups, too, can undergo analogous -shifts, as was demonstrated by the rearrangement of the o-lithiated N-(trimethylsilyl)aniline 63b to the o-(trimethylsilyl)anilines 65a,b.When a benzoyl and sulfonyl group can compete for the -shifts, as in the N-tosylated benzamide 47b, only the benzoyl group migrates.However, the migration tendency of the trimethylsilyl group equals that of the benzoyl group as was shown with the N-silylated benzamide 66b.
- Hellwinkel, Dieter,Laemmerzahl, Frank,Hofmann, Gunter
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p. 3375 - 3405
(2007/10/02)
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