67979-39-9Relevant articles and documents
Palladium-catalyzed carbonylation of iminoquinones and aryl iodides to access arylp-amino benzoates
Wang, Siqi,Wu, Xiao-Feng,Yao, Lingyun,Ying, Jun
supporting information, p. 8246 - 8249 (2021/10/12)
A palladium-catalyzed carbonylation of iminoquinones and aryl iodides has been developed for the construction of arylp-amino benzoates. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source, the reaction proceeded well to give various arylp-amino benzoates in good to excellent yields. Additionally, control experiments were conducted to gain more insights into the reaction mechanism.
Pd-Catalyzed Redox-Neutral C-N Coupling Reaction of Iminoquinones with Electron-Deficient Alkenes without External Oxidants: Access of Tertiary (E)-Enamines and Application to the Synthesis of Indoles and Quinolin-4-ones
Jillella, Raveendra,Raju, Selvam,Hsiao, Huan-Chang,Hsu, Day-Shin,Chuang, Shih-Ching
supporting information, p. 6252 - 6256 (2020/08/12)
A novel and efficient reductive N-alkenylation of iminoquinones with electron-deficient olefins has been successfully developed by Pd(II)-catalyzed redox-neutral reactions, which provides a synthesis of tertiary (E)-enamines. We further demonstrate that the tertiary enamines can be converted to multifarious N-heterocyclic compounds, indoles, and quinolones in good yields.
Mechanism of autoreduction of bis(4-methoxyphenyl)-oxoammonium perchlorate in aqueous alkali
Golubev,Sen
experimental part, p. 1313 - 1317 (2011/12/16)
Autoreduction of bis(4-methoxyphenyl)oxoammonium perchlorate in aqueous alkali follows a mechanism different from that generally accepted for diaryloxoammonium salts. Bis(4-methoxyphenyl)-oxoammonium cation undergoes hydrolysis to the corresponding quinone imine oxide and methanol, the latter gives rise to methoxide ion which reduces the oxoammonium cation to intermediate bis(4-methoxyphenyl)-hydroxylamine. The reaction of bis(4-methoxyphenyl) hydroxylamine with the initial cation yields bis-(4-methoxyphenyl)nitroxyl, and the quinone imine oxide undergoes disproportionation to N-(4-methoxyphenyl)-1,4- benzoquinone imine and oxidation products. Pleiades Publishing, Ltd., 2011.
Direct Nitrosation of Aromatic Hydrocarbons and Ethers with the Electrophilic Nitrosonium Cation
Bosch, Eric,Kochi, Jay K.
, p. 5573 - 5586 (2007/10/02)
Various polymethylbenzenes and anisoles are selectively nitrosated with the electrophilic nitrosonium salt NO(1+)BF4(1-) in good conversions and yields under mild conditions in which the conventional procedure (based on nitrile neutralization with strong acid) is ineffective.The reactivity patterns in acetonitrile deduced from the various time/conversions in Tables 2 and 3 indicate that aromatic nitrosation is distinctly different from those previously established for electrophilic aromatic nitration.The contrasting behavior of NO(1+) in aromatic nitrosation is ascribed to a rate-limiting deprotonation of the reversibly formed Wheland intermediate, which in the case of aromatic nitration with NO2(1+) occurs with no deuterium kinetic isotope effect.Aromatic nitroso derivatives (unlike the nitro counterpart) are excellent electron donors that are subject to a reversible one-electron oxidation at positive potentials significantly less than that of the parent polymethylbenzene or anisole.As a result, the series of nitrosobenzenes are also much better Broensted bases than the corresponding nitro derivatives, and this marked distinction, therefore, accounts for the large differentiation in the deprotonation rates of their respective conjugate acids (i.e.Wheland intermediates).
