260-94-6Relevant articles and documents
N-H Bond Formation in a Manganese(V) Nitride Yields Ammonia by Light-Driven Proton-Coupled Electron Transfer
Wang, Dian,Loose, Florian,Chirik, Paul J.,Knowles, Robert R.
, p. 4795 - 4799 (2019)
A method for the reduction of a manganese nitride to ammonia is reported, where light-driven proton-coupled electron transfer enables the formation of weak N - H bonds. Photoreduction of (saltBu)MnVN to ammonia and a Mn(II) complex has been accomplished using 9,10-dihydroacridine and a combination of an appropriately matched photoredox catalyst and weak Br?nsted acid. Acid-reductant pairs with effective bond dissociation free energies between 35 and 46 kcal/mol exhibited high efficiencies. This light-driven method may provide a blueprint for new approaches to catalytic homogeneous ammonia synthesis under ambient conditions.
Castellano et al.
, p. 3508,3511 (1973)
Copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(Arylamino)aryl]ethanones leading to acridone derivatives
Yu, Jipan,Yang, Haijun,Jiang, Yuyang,Fu, Hua
, p. 4271 - 4277 (2013)
Efficient copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C-H and acetyl C-C bonds with intramolecular formation of a diarylketone bond. The protocol uses inexpensive Cu(O2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as the oxidant, and the corresponding acridones with various functional groups were obtained in moderate to good yields. Acridone synthesis: Efficient copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C-H and acetyl C-C bonds with intramolecular formation of a diarylketone bond (see scheme). The protocol uses inexpensive Cu(O 2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as oxidant. The corresponding acridones with various functional groups were obtained in moderate to good yields. Copyright
Formation of Acridine from the Reaction of Dibenzazepine with Silver(I): Formation of an Aromatic Nitrenium Ion ?
Cann, Michael C.
, p. 1112 - 1113 (1988)
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A Simple Route to C-Functionalised Azaxylylenes and Diazaxylylenes
Fishwick, Colin W. G.,Storr, Richard C.,Manley, Paul W.
, p. 1304 - 1305 (1984)
o-Lithiation of t-butoxycarbonylaniline and 4-t-butoxycarbonylaminopyridine followed by reaction with aldehydes gives t-butoxycarbonylamino alcohols which are converted into azaxylylenes and diazaxylylenes on flash pyrolysis.
Oxidation of N-methyl-9-t-butylacridane by iodosylbenzene catalyzed by tetrakis(pentafluorophenyl) porphyrin iron(III). A tool to investigate the mechanism of the oxidative N-demethylation of aromatic tertiary amines
Baciocchi, Enrico,Lapi, Andrea
, p. 5425 - 5428 (1999)
The PhIO promoted oxidation of N-methyl-9-t-butylacridane (1) catalyzed by tetrakis(pentafluorophenyl) porphyrin iron(III) leads first to 9-t- butylacridane and then to acridine. It is suggested that 1 can represent a reliable machanistic probe to detect the intervention of radical cations in the oxidation of aromatic amines.
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Bernardi et al.
, p. 3575,3580 (1971)
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Photocatalytic degradation of antiepileptic drug carbamazepine with bismuth oxychlorides (BiOCl and BiOCl/AgCl composite) in water: Efficiency evaluation and elucidation degradation pathways
Meribout, Rayene,Zuo, Ying,Khodja, Amina Amine,Piram, Anne,Lebarillier, Stéphanie,Cheng, Jiushan,Wang, Cong,Wong-Wah-Chung, Pascal
, p. 105 - 113 (2016)
The heterogeneous photocatalytic degradation of carbamazepine (CBZ) was investigated in the presence of BiOCl/AgCl composite photocatalyst under simulated sunlight irradiation in water. BiOCl/AgCl composite showed higher photocatalytic activity than pure BiOCl for CBZ degradation. The photocatalytic mechanism analysis was based on byproducts identification by LC–MS-QTof and active species trapping or inhibiting experiments. The results revealed that the first step of the transformation mainly results in an electron transfer implying positive holes and to a lesser extent in hydroxyl radical's involvement. The enhanced photocatalytic performance of BiOCl/AgCl was proved to be related to the suitable conduction and valence band interaction that extends optical response range but also improves the efficient separation of photoinduced electron-hole pairs. BiOCl/AgCl composite totally removed CBZ from natural surface water after 30?min irradiation, suggesting its potential application to wastewater treatments. Eight intermediate products were identified demonstrating that CBZ transformation occurs through two main routes from CBZ radical cation, hydroxylation of ring (aromatic or seven membered rings), followed by further oxidation, rearrangement ring and hydroxylation.
New Gas Phase Reactions of Substituted Benzyl, Phenylaminyl, and Phenoxyl Radicals. Rearrangements to Fused 5- and 6-Membered Heterocyclic Systems
Cadogan, J. I. G.,Hickson, Clare L.,Hutchison, H. Susan,McNab, Hamish
, p. 643 - 644 (1985)
Flash vacuum pyrolysis studies of substituted benzyl, phenylaminyl, and phenoxyl radicals have revealed three new classes of reactions: formation of five-membered ring products via intramolecular abstracion of an aromatic hydrogen atom, formation of six-membered rings via spirodienyl radical intermediates, and isomerisation of o-phenoxybenzyl into o-benzylphenoxyl radicals and vice versa.
Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
Fiorio, Jhonatan L.,Rossi, Liane M.
, p. 312 - 318 (2021/01/29)
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of N-Heterocycles
Manna, Srimanta,Kong, Wei-Jun,B?ckvall, Jan-E.
supporting information, p. 13725 - 13729 (2021/09/08)
Herein, an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions is described. The dehydrogenation process, involving several electron-transfer steps, is inspired by oxidations occurring in the respiratory chain. An environmentally friendly and inexpensive iron catalyst together with a hydroquinone/cobalt Schiff base hybrid catalyst as electron-transfer mediator were used for the substrate-selective dehydrogenation reaction of various N-heterocycles. The method shows a broad substrate scope and delivers important heterocycles in good-to-excellent yields.