Triazenolysis of Alkenes: Aza-version of Ozonolysis

Abstract

Numerous applications of alkenes exist due to their abundance and versatility in chemical transformations. In this study, we present a unique and novel chemical transformation of alkenes, the aza-version of canonical ozonolysis reaction, which we termed as triazenolysis. This process offers a non-trivial and previously unfeasible synthetic disconnection, allowing the cleavage of a C=C double bond into two new C-N bonds in a reductive manner. We carefully examined the applicability of the reaction, finding that diverse cyclic alkenes are suitable for the developed process. Furthermore, we present an example of an acyclic alkene, illustrating the potential for expanding triazenolysis to other acyclic counterparts. Through DFT calculations, we explored the mechanism of the key step and demonstrated the significance of Lewis acid catalysis in achieving the desired transformation.