terminal alkynes

metal free

bond activation

text referenceadd description

direct arylation

cross-coupling reactions

cyclic carbonates

given article information

reaction

Journal of the American Chemical Society

Developing strategies enabling the modification of underlying molecular frameworks facilitates access to underexplored chemical spaces. Skeletal editing is an emerging technology for late-stage diversification of bioactive molecules. However, the current state of this knowledge remains undeveloped. This work describes a simple protocol that "inserts" a nitrogen atom into arylcycloalkenes to form the corresponding <i>N</i>-heterocycles. The use of an inexpensive cobalt catalyst under aqueous and open-air conditions makes this protocol very practical. Examples of late-stage modification of compounds of pharmaceutical interest and complex fused ring compounds further demonstrated the potentially broad applicability of this methodology.

Cobalt-Catalyzed Nitrogen Atom Insertion in Arylcycloalkenes