Direct oxidative cyanation based on the concept of site isolation
On the basis of the concept of site isolation, we have successfully demonstrated direct oxidative cyanation of various organic compounds, which even have higher oxidation potentials compared to that of cyanide, by using a polystyrene-supported quaternary ammonium cyanide. Copyright
Potassium ion cationized polyether cyanide [K+{PEG}CN-] as a novel cyanide source for oxidative cyanation of tertiary amines
Potassium ions cationized polyether cyanide [K+{PEG}CN-] was readily synthesized by mixing potassium cyanide and PEG400 at room temperature and used as a cost effective and comparatively safer alternative to the toxic sodium cyanide/acetic acid system for generating in situ HCN for the oxidative cyanation of tertiary amines with hydrogen peroxide using RuCl3 as catalyst. This method affords a facile approach to the synthesis of α-aminonitriles in high yields under solvent-free and acid-free reaction conditions.
Method for preparing alpha-aminonitrile and product and application thereof
The invention discloses a method for preparing alpha-aminonitrile, which comprises the following steps: by using tertiary amine and benzoyl cyanide as reactants, carrying out visible light irradiationin an organic solvent under the condition of oxygen or
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Paragraph 0061-0066
(2021/02/24)
Electron Donor-Acceptor Complex-Initiated Photochemical Cyanation for the Preparation of α-Amino Nitriles
An electron donor-acceptor complex-initiated α-cyanation of tertiary amines has been described. The reaction protocol provides a novel method to synthesize various α-amino nitriles under mild conditions. The reaction can proceed smoothly without the presence of photocatalysts and transition metal catalysts, and either oxidants are unnecessary or O2 is the only oxidant. The practicality of this method is showcased not only by the late-stage functionalization of natural alkaloid derivatives and pharmaceutical intermediate, but also by the applicability of a stop-flow microtubing reactor.
PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp2)-H or C(sp3)-H: Nitration via C-N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water
A novel nitration (via C(sp3)-N breaking/C(sp2)-N formation with CH3NO2) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO2 transfer from CH3NO2 to the aromatic group of the substrate is possible with careful selection of the solvent, NaX, and oxidant. In addition, the solvent-controlled C(sp2)-H functionalization can shift to an α-C(sp3)-H functionalization (cyanation or oxygenation) of the α-C(sp3)-H of cyclic amines.
Mudithanapelli, Chandrashekar,Dhorma, Lama Prema,Kim, Mi-Hyun
supporting information
(2019/05/07)
Oxidative Functionalization of Cyclic N -Arylamines with Nitromethane and TMSCN Using the T-HYDRO/ t -BuOK System
Tertiary cyclic N -arylamines react with nitromethane in the presence of the tert -butyl hydroperoxide (T-HYDRO)/ t -BuOK system to give β-nitroamines in up to 90% yield. When TMSCN is used in place of nitromethane, α-aminonitriles are obtained in up to 9
Rao, Gunda Ananda,Periasamy, Mariappan
p. 617 - 624
(2017/11/15)
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