The importance of nitrogen-containing heteroaromatic compounds is highlighted by their essential structural roles in pharmaceutical compounds. As a result, the need for rapid access to functionalized heteroaromatics plays a critical role in the drug discovery process. This project aims to leverage the Radical Smiles-Truce photocatalysis cascade to establish yields for two categories of starting materials with a sustainable approach: an externally and internally tethered olefin to an heteroaryl sulfone.