Kolb, Daniel and Friedmann, Kai and Koenig, Burkhard (2024) Tandem Synthesis of Benzylidenemalononitrile Derivatives in/on Water under Visible Light. CHEMCATCHEM, 16 (21). ISSN 1867-3880, 1867-3899
Full text not available from this repository. (Request a copy)Abstract
Tandem processes are valuable tools that allow to build molecular complexity while reducing waste production and the number of steps of synthetic routes. In this work, the in situ photooxidation of benzyl alcohols to the corresponding benzaldehydes is coupled with a Knoevenagel condensation for the preparation of benzylidenemalononitrile derivatives. In this rapid one-pot tandem process, sodium anthraquinone-1,5-disulfonate (SAS) and beta-alanine are employed as safe and inexpensive catalysts, while air is used as a terminal oxidant. Moreover, using water as reaction medium results in most cases in the precipitation of the target products, thus facilitating their isolation. Benzylidenemalononitrile derivatives are widely used as radical traps and as starting materials in Giese-type reactions. We report a tandem photooxidative process for the one-pot preparation of these products using water as reaction medium. In this cascade reaction, sodium anthraquinone-1,5-disulfonate is employed as a light-induced HAT catalyst, while beta-alanine acts as a green and inexpensive organocatalyst. In most cases, the formed products precipitate and can be filtered, resulting in an operationally simple procedure. image
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | KNOEVENAGEL CONDENSATION; OXIDATION; TYRPHOSTINS; GREEN; TRANSFORMATIONS; MALONONITRILE; CHEMISTRY; KINETICS; ALCOHOL; SYSTEM; Photooxidation; Water; Tandem; Benzylidenemalononitrile; Benzyl alcohol |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 17 Jul 2025 09:50 |
| Last Modified: | 17 Jul 2025 09:50 |
| URI: | https://pred.uni-regensburg.de/id/eprint/63549 |
Actions (login required)
 |
View Item |
