Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations

Area of Science:

• Organic Chemistry
• Electrochemistry
• Synthetic Methodology

Background:

• Cycloalkanols are versatile cyclic alcohols.
• Functionalization of cycloalkanols can be challenging.
• Existing methods may lack efficiency or scope.

Purpose of the Study:

• To develop a novel electrochemical method for cycloalkanol functionalization.
• To explore the use of diverse nucleophiles in this transformation.
• To demonstrate the scalability and efficiency of the developed method.

Main Methods:

• Electrochemical deconstructive functionalization of cycloalkanols.
• Utilized alcohols, carboxylic acids, and N-heterocycles as nucleophiles.
• Employed single-pass continuous flow for gram-scale synthesis.

Main Results:

• Successfully synthesized 36 examples of remotely functionalized ketone products.
• Demonstrated broad substrate scope across various cycloalkanol ring sizes and substituents.
• Achieved increased productivity using continuous flow compared to batch processing.

Conclusions:

• The developed electrochemical approach offers an efficient route to functionalized ketones.
• The method is versatile, accommodating a wide range of substrates and nucleophiles.
• Continuous flow processing enables scalable and productive synthesis.