Divergent C-H Amidations and Imidations by Tuning Electrochemical Reaction Potentials

Area of Science:

• Organic Chemistry
• Electrochemistry
• Synthetic Methodology

Background:

• Electrochemical C-H functionalization offers a sustainable alternative to traditional methods, reducing reliance on transition metals and oxidants.
• Developing tunable electrochemical methods is crucial for expanding the scope of C-H activation reactions.
• Cyclic amines and imines are prevalent scaffolds in pharmaceuticals and materials science.

Purpose of the Study:

• To develop an electrochemically tunable method for divergent synthesis of cyclic amines and imines.
• To achieve selective C-H amidations and imidations using electrochemistry.
• To explore the utility of the synthesized motifs in late-stage modifications.

Main Methods:

• Electrochemical synthesis with tunable reaction potentials.
• Cyclic voltammetry and chronopotentiometry for mechanistic studies.
• Paired electrolysis to assess atom economy.

Main Results:

• Divergent formation of cyclic amines or imines achieved by varying applied potentials.
• Selective C-H amidations and imidations successfully performed.
• Synthesis of five- to seven-membered sulfonamide motifs demonstrated.

Conclusions:

• The developed electrochemical method provides a versatile and sustainable route to cyclic amines and imines.
• The method's tunability allows for control over reaction outcomes.
• Synthesized sulfonamide motifs are suitable for late-stage functionalization in drug discovery and development.