African Journal of
Pure and Applied Chemistry

  • Abbreviation: Afr. J. Pure Appl. Chem.
  • Language: English
  • ISSN: 1996-0840
  • DOI: 10.5897/AJPAC
  • Start Year: 2007
  • Published Articles: 368

Article in Press

Oxidative Carbon-Carbon Bond Formation Using Nitromethane As A Solvent And A Reagent Via Functionalization Of Heterocyclic Amine

Collins O. Owino, Samuel S. Libendi, Paul M. Guyo

  •  Received: 05 March 2022
  •  Accepted: 30 March 2023
???substituted Heterocyclic amines account for the main structural skeleton for organic synthesis and constitute adaptable pattern found in numerous medicinal and biological compounds of importance. The development of electrochemical anodic oxidation reactions in the synthesis of advanced ?-substituted heterocycles is highly desirable. The main purpose of this research was to ascertain the functionality of oxidation at the anodes and consecutive reaction for selective functionalization of derivatives of cyclic amine using graphite electrodes and nitromethane as a solvent followed by carbon-carbon bond coupling using carbon nucleophile with nitromethane as a reagent and triethylamine as a base. The study involved the protection of cyclic amines with different protecting groups. An ?-functionalization of Nitrogen-protected heterocyclic amines was done using a straight electrolysis method utilizing CH3NO2 as a solvent followed by C-C bond coupling stirring in nitromethane with 2eq. of triethylamine as a base in an undivided two step cell. Nitrogen-protected heterocyclic amines with no substituent were simply alkylated at the ?-position using a complete cell with up to 93% yields; moreover, ?-alkylation of ?-substituted piperidine also took place easily with high yield up to 98%. In conclusion, this paper revealed the feasibility of utilizing an electrolysis method to carry out C-C bond coupling utilizing CH3NO2 as both a solvent for the generation of iminium ions at room temperature and a reagent to generate nitronate ions to act as a nucleophile to form C-C bonds.

Keywords: oxidative carbon - carbon bond formation; nitromethane; funtionalization