Uncanonical Semireduction of Quinolines and Isoquinolines via Regioselective HAT-Promoted Hydrosilylation

Heterocycles are the backbone of modern medical chemistry and drug development. The derivatization of an olefin inside aromatic rings represents an ideal approach to access functionalized saturated heterocycles from abundant aromatic building blocks. Here, we report an operationally simple, efficient, and practical method to selectively access hydrosilylated and reduced N-heterocycles from bicyclic aromatics via a key diradical intermediate. This approach is expected to facilitate complex heterocycle functionalizations that enable access to novel medicinally relevant scaffolds.

Automated summary

Heterocycles play a crucial role in modern medical chemistry and drug development. In this study, a simple and efficient method was developed to selectively synthesize hydrosilylated and reduced N-heterocycles from abundant aromatic building blocks. This approach has the potential to facilitate the synthesis of novel medicinally relevant scaffolds.