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Electrocatalytic C-N Coupling via Anodically Generated Hypervalent Iodine Intermediates.

Asim Maity¹, Brandon L Frey¹, Nathanael D Hoskinson¹

¹Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.

Journal of the American Chemical Society

|March 5, 2020

Summary

This study introduces metal-free hypervalent iodine electrocatalysis for efficient and sustainable organic synthesis. Anodic generation of hypervalent iodine intermediates enables novel C-H and N-H coupling reactions, advancing synthetic electrochemistry.

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Area of Science:

Organic Chemistry
Electrochemistry
Sustainable Synthesis

Background:

Electrosynthetic chemistry offers sustainable routes for organic synthesis.
Hypervalent iodine compounds are versatile reagents in organic transformations.

Purpose of the Study:

To develop a metal-free hypervalent iodine electrocatalysis system.
To enable efficient C-H/N-H coupling reactions using electrochemistry.
To provide mechanistic insights into hypervalent iodine-mediated electrochemistry.

Main Methods:

Anodic oxidation of aryl iodides to generate hypervalent iodine intermediates.
Utilizing acetate ions for stabilization of transient intermediates.
Applying the developed system to intra- and intermolecular C-N bond-forming reactions.

Main Results:

Demonstrated effective coupling of interfacial electron transfer with oxidative C-H/N-H coupling.
Showcased applicability in both intramolecular and intermolecular C-N bond formation.
Identified a transient I(II) intermediate stabilized by acetate ions.

Conclusions:

This work presents the first metal-free hypervalent iodine electrocatalysis for C-H functionalization.
The findings offer mechanistic understanding for future development of hypervalent iodine mediators in synthetic electrochemistry.
This approach enhances the efficiency and sustainability of organic synthesis.