Project No. | LZP-2021/1-0595 |
|---|---|
Project coordinator | Latvian Institute of Organic Synthesis (LIOS)
|
Project manager | Dr. Igors Sokolovs (LIOS) |
Implementation period | 36 months (2022-2024) |
Total cost
| 299 999,70 EUR |
The scientific objective of this research project is the development of environmentally friendly, sustainable, and scalable synthetic methodologies for electrochemical production of stabilized organo-λ3-bromanes using divided electrochemical cell and electrochemical flow reactor.
Successful implementation of the project will result in the development of an inexpensive, environmentally benign, and safe method for obtaining organo-λ3-bromanes. This will enable further investigation of the propertie of these compounds and their application in organic chemistry as well as development of biologically active substances and smart materials.
The developed method is intended to be transferred to a continuous flow electrochemical cell, which will, if necessary, enable the industrial production of organo- λ3-bromanes.
Project Progress
The following research activities were carried out during the reporting period:
- Optimization studies for the electrochemical oxidation of ethyl 2-bromobenzoate (WP1);
- Synthesis of aryl bromides with different ortho-chelating groups (WP1).
Publication date 05.04.2022
The following research activities were carried out during the reporting period:
- Electrochemical oxidation of different aryl bromides and reaction product identification (WP1);
- The development of method for electrochemical generation of dimeric λ3-bromane (WP1).
Publication date 05.07.2022
The following research activities were carried out during the reporting period:
- Synthesis of a series of bromine(III) congeners from dimeric λ3-bromane (WP1);
- Investigation of electrochemical properties of prepared λ3-bromanes (WP1);
- Preliminary studies of chemical properties of dimeric λ3-bromane (WP1).
Publication date 04.10.2022
The following research activities were carried out during the reporting period:
- The development of method for photoinduced Minisci-type heteroarylation with dimeric λ3-bromane (WP1);
- The development of method for late-stage oxidative functionalization of complex natural products and pharmaceuticals with dimeric λ3-bromane (WP1).
Publication date 03.01.2023
The following research activities were carried out during the reporting period:
- Initial investigation of photoinduced Minisci-type heteroarylation reaction mechanism (WP1);
- Writing and submitting a publication manuscript on the Electrochemical Synthesis of Dimeric λ3-Bromane (WP3).
Publication date 04.04.2023
The following research activities were carried out during the reporting period:
- Optimization studies for the Minisci-type borylation (WP1);
- Synthesis of aryl bromides with longer conjugated bond system (WP1);
- Participation and poster presentation at the 7th International Conference on Hypervalent Iodine Chemistry (ICHIC 7) conference (Igors Sokolovs, WP3).
Publication date 04.07.2023
The following research activities were carried out during the reporting period:
– Identification of by-products in Minisci-type borylation and further optimization of the reaction with attempts to avoid their formation. (WP1)
– Attempts at electrochemical oxidation of prepared aryl bromides with longer conjugated bond system and preparation of other planned aryl bromides (WP1)
Publication date 05.10.2023
The following research activities were carried out during the reporting period:
– Continued synthesis of l3-bromanes with extended conjugated bond systems and study of their photochemical properties (WP1)
– Initial investigation of electrochemical oxidation/cyclization of 1,1′-dibromobiphenil (WP1)
–An invited lecture at 244th ECS (Electrochemical Society) Meeting (Igors Sokolovs, WP3).
Publication date 04.01.2024
The following research activities were carried out during the reporting period:
– Optimization of reaction conditions for electrochemical oxidation/cyclization of 1,1′-dibromobiphenil in an undivided electrochemical cell (WP1)
– Preparation of a model compound for the generation of λ3-bromane under continuous flow electrochemical oxidation conditions (WP2)
Publication date 04.04.2024
The following research activities were carried out during the reporting period:
– Optimization of reaction conditions for electrochemical oxidation/cyclization of 1,1′-dibromobiphenil in a divided electrochemical cell (WP1)
– Initial experiments on continuous flow electrochemical generation of λ3-bromane (WP2)
Publication date 04.07.2024
The following research activities were carried out during the reporting period:
– Electrochemical oxidation/cyclization of 1,1′-dibromobiphenil with two ethoxycarbonyl chelating groups (WP1)
– Further optimization of reaction conditions for the generation of λ3-bromane under continuous flow electrochemical oxidation conditions (WP2)
–Participation and poster presentation at the Balticum Organicum Syntheticum 2024 (BOS 2024) conference (Andrejs Savkins, WP3).
Publication date 03.10.2024
The following research activities were carried out during the reporting period:
– Electrochemical oxidation/cyclization of 1,1′-dibromobiphenil with one ethoxycarbonyl chelating group (WP1)
– Writing and submitting a publication manuscript on the Electrochemical Synthesis of Cyclic Biaryl λ3-Bromanes (WP3).
Publication date 03.01.2025