30926-00-2Relevant academic research and scientific papers
Cascade One-Pot Synthesis of Orange-Red-Fluorescent Polycyclic Cinnolino[2,3-f]phenanthridin-9-ium Salts by Palladium(II)-Catalyzed C?H Bond Activation of 2-Azobiaryl Compounds and Alkenes
Jayakumar, Jayachandran,Vedarethinam, Guganchandar,Hsiao, Huan-Chang,Sun, Shang-You,Chuang, Shih-Ching
, p. 689 - 694 (2019/11/22)
Quaternary ammonium salts were synthesized in moderate to good yields through double oxidative C?H bond activation on azobenzenes. The mechanism of the highly regioselective reaction of 2-azobiaryls with alkenes to give orange-red-fluorescent cinnolino[2,
Synergistic combination of visible-light photo-catalytic electron and energy transfer facilitating multicomponent synthesis of β-functionalized α,α-diarylethylamines
Wu, Yanan,Zhang, Yipin,Jiang, Mingjie,Dong, Xunqing,Jalani, Hitesh B.,Li, Guigen,Lu, Hongjian
supporting information, p. 6405 - 6408 (2019/06/07)
A synthetic strategy with the visible-light photo-catalytic synergistic combination of electron and energy transfer processes has been developed. The mild reaction conditions allow the radical-radical cross-coupling phenomenon for the multicomponent synthesis of β-arylsulfonyl(diarylphosphinoyl)-α,α-diarylethyl-amines from readily available arylsulfinic acids (diarylphosphine oxides), 1,1-diarylethylenes and arylazides.
Catalytic Nitrene Homocoupling by an Iron(II) Bis(alkoxide) Complex: Bulking Up the Alkoxide Enables a Wider Range of Substrates and Provides Insight into the Reaction Mechanism
Yousif, Maryam,Wannipurage, Duleeka,Huizenga, Caleb D.,Washnock-Schmid, Elizabeth,Peraino, Nicholas J.,Ozarowski, Andrew,Stoian, Sebastian A.,Lord, Richard L.,Groysman, Stanislav
supporting information, p. 9425 - 9438 (2018/08/17)
The reaction of HOR′ (OR′ = di-t-butyl-(3,5-diphenylphenyl)methoxide) with an iron(II) amide precursor forms the iron(II) bis(alkoxide) complex Fe(OR′)2(THF)2 (2). 2 (5-10 mol %) serves as a catalyst for the conversion of aryl azides
A practical synthesis of azobenzenes through oxidative dimerization of aromatic amines using tert-butyl hypoiodite
Takeda, Youhei,Okumura, Sota,Minakata, Satoshi
supporting information, p. 1029 - 1033 (2013/05/09)
A straightforward, convenient, and efficient synthetic method of azobenzenes through oxidative dimerization of aromatic amines using a unique and cost-effective iodinating reagent is described. This new method allows for easy access to both of symmetrical and unsymmetrical azobenzenes under extremely mild conditions. Georg Thieme Verlag Stuttgart. New York.
Oxidative dimerization of (hetero)aromatic amines utilizing t-BuOI leading to (hetero)aromatic azo compounds: Scope and mechanistic studies
Okumura, Sota,Lin, Chun-Hsuan,Takeda, Youhei,Minakata, Satoshi
, p. 12090 - 12105 (2014/01/06)
A straightforward synthetic method of both symmetric and unsymmetric aromatic azo compounds through an efficient and cross-selective oxidative dimerization of aromatic amines using tert-butyl hypoiodite (t-BuOI) under metal-free and mild conditions has been developed. This method was also found applicable to the synthesis of heteroaromatic azo compounds. The spectroscopic study indicates the involvement of N,N-diiodoanilines in the oxidative reaction as the key intermediate.
Photochemistry with laser radiation in condensed phase using miniaturized photoreactors
Bremus-Koebberling, Elke,Gillner, Arnold,Avemaria, Frank,Rethore, Celine,Braese, Stefan
experimental part, p. 1213 - 1218 (2012/09/22)
Miniaturized microreactors enable photochemistry with laser irradiation in flow mode to convert azidobiphenyl into carbazole with high efficiency.
Oxidative dimerization of aromatic amines using tBuOI: Entry to unsymmetric aromatic azo compounds
Takeda, Youhei,Okumura, Sota,Minakata, Satoshi
supporting information; experimental part, p. 7804 - 7808 (2012/09/05)
It's all the hype: An oxidative dimerization reaction of aromatic amines utilizing tert-butyl hypoiodite (tBuOI) under mild reaction conditions leads to aromatic azo compounds (see scheme). The method allows access to unsymmetric aromatic azo compounds, which are difficult to prepare by conventional synthetic methods, in a selective manner. Copyright
Chemical Consequences of Arylnitrenes in the Crystalline Environment
Sasaki, Akito,Mahe, Loic,Izuoka, Akira,Sugawara, Tadashi
, p. 1259 - 1275 (2007/10/03)
UV photolysis of powdered crystals of several aryl azides at cryogenic temperatures afforded azo compounds predominantly. In the cases of p-(N-methylacetamido)phenyl azide and 2-azidobiphenyl, a CH insertion product or a carbazole was formed, competing with azo formation. These products can be considered to be formed through topotactic processes when the crystal structures are taken into account. The arylnitrenes generated in the azide crystals were monitored by ESR spectroscopy; they turned out to have extremely long half life-times, compared with those in the gas phase or in solution. Such high kinetic stabilities are ascribed to the inert environment around the generated nitrenes. The decay process of arylnitrenes in the initial stage obeyed a pseudo-first order kinetics; activation parameters were evaluated by Arrhenius plots. The activation enthalpies and entropies indicate that the diffusional processes of arylnitrenes may be the vital factors determining the kinetic stability and the product distribution in the crystalline environment.
LDA-promoted decomposition of benzenesulfenamides. A route to aminyl radicals by dioxygen oxidation of lithium amides
Barbieri, Anna,Montevecchi, Pier Carlo,Nanni, Daniele,Navacchia, Maria Luisa
, p. 13255 - 13264 (2007/10/03)
The LDA-promoted decomposition of N-monosubstituted sulfenamides 1a-d occurs through the formation of thioaminyl anions, which undergo oxidation either at sulfur, with formation of sulfonamides, or at nitrogen, with formation of thioaminyl radicals, depending on the nature of the 4'-substituent. The reaction of N,N-disubstituted sulfenamides 1e-h proceeds through the intermediacy of a lithium complex capable of generating aminyl radicals via sulfenyl group transfer to the di-iso-propylamido anion and subsequent aerial oxidation of the resulting lithium amides 3e-h.
Metathesis and reduction reactions of nitroso compounds with metal carbenes and metal carbonyls
Herndon, James W.,McMullen, Leonard A.
, p. 83 - 102 (2007/10/02)
Reaction of nitroso compounds with metal-carbene complexes and metal carbonyls has been investigated.These reactions lead to reduction of the nitroso compounds, primarily to the corresponding azo- and azoxy compounds.Metal-nitrene complexes have been proposed as intermediates in these reactions.These intermediates couple rapidly with the unreacted nitroso compound, or enter into nitrene-like reactions with external or internal trapping agents.Reaction of metal carbonyls with nitrosoarenes and photolysis has been found to be an effective method for the reduction of nitrosoarenes to azoxyarenes, with few problems resulting from overreduction to amines or azo compounds.
