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Cobalt-Catalyzed Nitrogen Atom Insertion in Arylcycloalkenes.

Juanjuan Wang¹, Hong Lu¹, Yi He¹

¹Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710069, China.

Journal of the American Chemical Society

|November 30, 2022

Summary

This study introduces a practical method for skeletal editing, inserting nitrogen atoms into arylcycloalkenes to create N-heterocycles. This advance expands chemical diversity for drug discovery and complex molecule synthesis.

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Synthetic Chemistry

Background:

Skeletal editing is a key strategy for late-stage diversification of bioactive molecules.
Accessing underexplored chemical spaces is crucial for discovering novel therapeutics.
Current skeletal editing methods are limited, necessitating new protocols.

Purpose of the Study:

To develop a simple and practical protocol for skeletal editing.
To enable the late-stage diversification of complex organic molecules.
To introduce a nitrogen atom into arylcycloalkenes, forming N-heterocycles.

Main Methods:

Utilized an inexpensive cobalt catalyst.
Performed the reaction under aqueous and open-air conditions.
Applied the protocol to arylcycloalkenes for N-heterocycle synthesis.

Main Results:

Successfully demonstrated a simple protocol for N-heterocycle formation via nitrogen insertion.
Showcased the late-stage modification of pharmaceutical compounds.
Validated the broad applicability using complex fused ring systems.

Conclusions:

The developed protocol offers a practical and efficient route to N-heterocycles.
This skeletal editing strategy significantly expands accessible chemical space.
The method holds potential for drug discovery and synthesis of complex molecules.