Green electrosynthesis of bis(indolyl)methane derivatives in deep eutectic solvents
View abstract on PubMed
Summary
This summary is machine-generated.A novel green synthesis method for bis(indolyl)methane derivatives was developed using electrochemistry in deep eutectic solvents. This efficient approach offers mild conditions, short reaction times, and high yields for various substituted aromatic aldehydes.
Area Of Science
- Green Chemistry
- Organic Synthesis
- Electrochemistry
Background
- Traditional synthesis of bis(indolyl)methane derivatives often involves harsh conditions and hazardous solvents.
- Deep eutectic solvents (DES) offer a sustainable and environmentally friendly alternative to conventional solvents and electrolytes.
- Electrochemical synthesis provides a controlled and efficient method for organic transformations.
Purpose Of The Study
- To develop a novel, green, and efficient electrochemical method for synthesizing bis(indolyl)methane derivatives.
- To explore the use of deep eutectic solvents as a reaction medium for electrochemical synthesis.
- To optimize reaction parameters and investigate the scope of the developed method.
Main Methods
- Electrochemical bisarylation reaction was employed for the synthesis.
- Deep eutectic solvents, specifically ethylene glycol/choline chloride (2:1 ratio), were used as the reaction medium.
- Graphite and platinum electrodes served as cathode and anode, respectively.
- Reaction conditions including time, current, solvent, and electrode materials were systematically studied.
Main Results
- The optimized reaction conditions were 80°C for 45 minutes using ethylene glycol/choline chloride.
- High product yields were achieved with a wide range of substituted aromatic aldehydes (electron-donating and electron-withdrawing).
- The electrochemical method in DES demonstrated superior efficiency compared to conventional heating in DES, yielding higher product amounts in less time.
- The reaction mechanism was proposed and supported by cyclic voltammetry studies.
Conclusions
- A new, green, and efficient electrochemical method for synthesizing bis(indolyl)methane derivatives in deep eutectic solvents has been successfully developed.
- This method offers significant advantages, including mild conditions, short reaction times, high yields, and broad substrate scope.
- The electrochemical approach in DES is a promising and sustainable alternative for the synthesis of valuable bis(indolyl)methane compounds.
Related Concept Videos
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Electrocyclic reactions are highly stereospecific. For a substituted polyene, the stereochemical outcome...
Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
This method is a nucleophilic substitution reaction. The two alcohol molecules...
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

