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Esterification of Aryl/Alkyl Acids Catalysed by
Klara Čebular1,2,3, Bojan Đ Božić4,5, Stojan Stavber6,7,8
1Centre of Excellence for Integrated Approaches in Chemistry and Biology of Proteins, Jamova 39, 1000 Ljubljana, Slovenia. klara.cebular@ijs.si.
N-bromosuccinimide (NBS) efficiently catalyzes direct esterification of carboxylic acids. This metal-free method offers high yields and simple procedures for synthesizing aromatic and alkyl esters.
Area of Science:
- Organic Chemistry
- Green Chemistry
Background:
- N-halosuccinimides (NXSs) are common halogenation reagents.
- Direct esterification is a crucial transformation in organic synthesis.
Purpose of the Study:
- To identify the most effective NXS catalyst for direct esterification.
- To develop a metal-free, efficient, and scalable esterification protocol.
Main Methods:
- Screening of various N-halosuccinimides (NXSs) as catalysts.
- Direct esterification of aryl and alkyl carboxylic acids under neat conditions.
- Optimization of reaction parameters for efficiency and selectivity.
Main Results:
- N-bromosuccinimide (NBS) demonstrated superior catalytic activity and selectivity.
- High yields (up to 100%) achieved for a wide range of aromatic and alkyl esters.
- The protocol is metal-free, air- and moisture-tolerant, facilitating simple isolation and scale-up.
Conclusions:
- N-bromosuccinimide is an excellent catalyst for direct esterification.
- The developed method offers a sustainable and efficient route to ester synthesis.
- A catalyst recycling protocol was successfully proposed.
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