Electrochemical Benzylic C(sp³)-H Acyloxylation

Area of Science:

• Organic Chemistry
• Sustainable Chemistry

Background:

• C(sp³)-H functionalization is vital for pharmaceuticals and agrochemicals.
• Anodic oxidation offers a pathway to generate reactive intermediates like benzylic cations.
• Developing efficient and sustainable methods for C-H functionalization remains a significant challenge.

Purpose of the Study:

• To develop a sustainable method for C(sp³)-H functionalization.
• To explore the use of carboxylic acids as nucleophiles in anodic oxidation reactions.
• To synthesize functionalized benzylic esters via a novel route.

Main Methods:

• Electrochemical oxidation of secondary benzylic substrates.
• In situ nucleophilic attack by carboxylic acids.
• Flow chemistry for gram-scale synthesis.

Main Results:

• Successful synthesis of benzylic esters from secondary benzylic substrates and carboxylic acids.
• Demonstration of the method's efficiency and scalability.
• Gram-scale production achieved using flow electrochemistry.

Conclusions:

• Carboxylic acids are effective nucleophiles for anodic oxidation of C(sp³)-H bonds.
• This method provides a sustainable and efficient route to valuable benzylic esters.
• Flow electrochemistry enables scalable and practical synthesis for industrial applications.