Chiral S(VI) platform unifies selective C–H amination of complex molecules and alkane feedstocks
- Tuan Anh Trinh
- Derek B. Hu
- Anna J. Kenny
- Ethan M. Warrington
- Stanislav Cherempei
- Ilia A. Guzei
- Jennifer M. Schomaker
2026-04-23
Complex molecules and simple alkanes pose distinct challenges for catalyst-controlled carbon-hydrogen (C–H) functionalizations. Whereas densely functionalized scaffolds require precise targeting among multiple reactive sites while tolerating sensitive functionalities, unactivated substrates that lack directing groups require selective activation of exceptionally inert, nearly identical C–H bonds. In this work, we addressed both challenges by repurposing a classic chiral auxiliary into a unified, selective, and predictable C–H amination platform mediated by silver catalysis and chiral sulfur(VI) nitrene precursors. This system enables stereodivergent, late-stage aminations of activated C–H bonds with broad functional group tolerance and compatibility with aqueous conditions while also mediating mild, selective aminations of chemical feedstocks. The sulfur(VI) motif functions as a modular, stereodefined, and medicinally relevant synthetic linchpin for rapid library diversification, enabling both target- and diversity-oriented synthesis.