Visible‐Light‐Enabled Direct Decarboxylative N‐Alkylation
| Autor: | Vu T. Nguyen, Hadi D. Arman, Oleg V. Larionov, Viet D. Nguyen, Graham C. Haug, Ngan T. H. Vuong, Hang T. Dang |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Aniline Compounds
Alkylation Tandem 010405 organic chemistry Chemistry Decarboxylation General Medicine General Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Combinatorial chemistry Article Catalysis 0104 chemical sciences Heterocyclic Compounds Photocatalysis Acridines Amines Oxidation-Reduction Amination Visible spectrum |
| Zdroj: | Angew Chem Int Ed Engl |
| ISSN: | 1521-3773 1433-7851 |
| Popis: | The development of efficient and selective C-N bond-forming reactions from abundant feedstock chemicals remains a central theme in organic chemistry owing to the key roles of amines in synthesis, drug discovery, and materials science. Herein, we present a dual catalytic system for the N-alkylation of diverse aromatic carbocyclic and heterocyclic amines directly with carboxylic acids, by-passing their preactivation as redox-active esters. The reaction, which is enabled by visible-light-driven, acridine-catalyzed decarboxylation, provides access to N-alkylated secondary and tertiary anilines and N-heterocycles. Additional examples, including double alkylation, the installation of metabolically robust deuterated methyl groups, and tandem ring formation, further demonstrate the potential of the direct decarboxylative alkylation (DDA) reaction. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text