# Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes

## TL;DR

Scientists developed a new method to convert polycyclic arenols into N-heteroarenes by swapping carbon atoms with nitrogen, enabling the creation of complex aromatic structures.

## Contribution

A novel skeletal editing strategy for carbon-to-nitrogen transmutation in polycyclic arenol frameworks is introduced.

## Key findings

- The method enables selective nitrogen insertion into C–C bonds of arenol frameworks via azidative dearomatization and aryl migration.
- The approach allows streamlined assembly of complex polycyclic heteroaromatics with broad functional group tolerance.
- Transformations of the products showed potential in materials chemistry, including synthesis of complex biheteroarene skeletons.

## Abstract

Developing skeletal editing tools is not a trivial task, and realizing the corresponding single-atom transmutation in a ring system without altering the ring size is even more challenging. Here, we introduce a skeletal editing strategy that enables polycyclic arenols, a highly prevalent motif in bioactive molecules, to be readily converted into N-heteroarenes through carbon–nitrogen transmutation. The reaction features selective nitrogen insertion into the C–C bond of the arenol frameworks by azidative dearomatization and aryl migration, followed by ring-opening, and ring-closing (ANRORC) to achieve carbon-to-nitrogen transmutation in the aromatic framework of the arenol. Using widely available arenols as N-heteroarene precursors, this alternative approach allows the streamlined assembly of complex polycyclic heteroaromatics with broad functional group tolerance. Finally, pertinent transformations of the products, including synthesis complex biheteroarene skeletons, were conducted and exhibited significant potential in materials chemistry.

Developing skeletal editing tools, especially to realize the single-atom transmutation in a ring system without altering the ring size is challenging. Here, the authors introduce a skeletal editing strategy that enables polycyclic arenols to be readily converted into N-heteroarenes through carbon–nitrogen transmutation.