Electrochemical Oxidative Carbon-Atom Difunctionalization: Towards Multisubstituted Imino Sulfide Ethers

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Electrochemistry

Background:

• Imino sulfide ethers (N(sp2)=C(sp2)-O/S) are crucial motifs in functional molecules and natural products.
• The synthesis of imino sulfide ethers is challenging due to their acid sensitivity.

Purpose of the Study:

• To develop an unprecedented electrochemical method for synthesizing multisubstituted imino sulfide ethers.
• To overcome the limitations of existing synthetic routes, particularly acid sensitivity.

Main Methods:

• Electrochemical oxidative carbon-atom difunctionalization of isocyanides.
• Reaction of isocyanides with mercaptans and alcohols under metal-free and oxidant-free conditions.

Main Results:

• Successful synthesis of a series of novel multisubstituted imino sulfide ethers.
• High stereoselectivities and excellent functional-group tolerance were achieved.
• The method demonstrated good efficiency in large-scale synthesis and allowed for further product derivatization.

Conclusions:

• The developed electrochemical method provides an efficient and versatile route to imino sulfide ethers.
• This approach avoids harsh acidic conditions, broadening the scope for synthesizing acid-sensitive compounds.
• The methodology is scalable and amenable to further synthetic modifications.