- O-iodoxybenzoic acid mediated N-arylation of aromatic amines by using arylhydrazines as the arylating counterpart
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Through free-radical trapping experiments we have established, for the first time, the combination of arylhydrazines with o-iodoxybenzoic acid (IBX) for the generation of aryl free radicals. On the basis of this finding, a method was developed for the N-arylation of aromatic amines under mild conditions (base-free, -5 °C) by using arylhydrazines as the arylating counterpart and arylamines. The scope of this method was demonstrated by using a number of arylhydrazines and arylamines, which gave the N-arylated amines in good yields. Through free-radical trapping experiments, the present work describes the combination of arylhydrazines with o-iodoxybenzoic acid (IBX) for the generation aryl free radicals. This finding is exploited in the development of a mild method for the N-arylation of arylamines by using arylhydrazines as the arylating agents. The scope of this method is demonstrated through a number of examples. Copyright
- Jadhav, Ravindra R.,Huddar, Sameerana N.,Akamanchi, Krishnacharya G.
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- Copper-Mediated C-N Coupling of Arylsilanes with Nitrogen Nucleophiles
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A method for the oxidative coupling of arylsilanes with nitrogen nucleophiles is reported. This method occurs with a broad range of heptamethyltrisiloxylarenes and nitrogen nucleophiles, proceeds with the arylsilane as limiting reagent, and does not require a fluoride activator with electron-poor arylsilanes. The combination of this method with C-H silylation generates arylamines from unactivated arenes with site selectivity controlled by steric effects. This combination of steps gives direct access to many compounds that cannot be accessed via alternative C-H functionalization methods, including direct C-H amination or the combination of C-H borylation and amination.
- Morstein, Johannes,Kalkman, Eric D.,Cheng, Chen,Hartwig, John F.
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p. 5244 - 5247
(2016/11/02)
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- N,N-diacylpiperazine tachykinin antagonists
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Diacylpiperazines of general structure STR1 are tachykinin receptor antagonists useful in the treatment of inflammatory diseases, pain or migraine, and asthma, and calcium channel blockers useful in the treatment of cardiovascular conditions such as angina, hypertension or ischemia.
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- Micellar Catalysis of the Basic Hydrolysis of Amides. 4. Substituted N,N-Diphenylbenzamides
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The cytalysis of the basic hydrolysis of a series of N-aryl-N-phenylbenzamides (1) and a series of substituted N,N-diphenylbenzamides (2) by micelles of cetyltrimethylammonium bromide (ctab) has been studied.On the basis of the effects of substituents on the aromatic ring attached to the nitrogen atom, a mechanistic change on transfer from water to a micellar environment is proposed.In water the mechanism involves rate-determining solvent-assisted carbon-nitrogen bond breaking (mechanism B), while in the presence of micelles of ctab, a rate-determining attack of hydroxide ion (mechanism C) is proposed.Reasons for mechanistic change are discussed.
- Broxton, Trevor J.,Fernando, Denise R.,Rowe, Jeffrey E.
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p. 3522 - 3525
(2007/10/02)
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