Controlling One- or Two-Electron Oxidation for Selective Amine Functionalization by Alternating Current Frequency.
J Am Chem Soc
; 144(22): 9874-9882, 2022 06 08.
Article
em En
| MEDLINE
| ID: mdl-35622985
ABSTRACT
Here, we report a unique electrosynthetic method that enables the selective one-electron oxidation of tertiary amines to generate α-amino radical intermediates over two-electron oxidation to iminium cations, providing easy access to arylation products by simply applying an optimal alternating current (AC) frequency. More importantly, we have discovered an electrochemical descriptor from cyclic voltammetry studies to predict the optimal AC frequency for various amine substrates, circumventing the time-consuming trial-and-error methods for optimizing reaction conditions. This new development in AC electrolysis provides an alternative strategy to solving challenging chemoselectivity problems in synthetic organic chemistry.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Elétrons
/
Aminas
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2022
Tipo de documento:
Article
País de afiliação:
Estados Unidos