Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds

Abstract

Lighting the way to drug labeling It is important during drug development to study how candidate compounds get absorbed and broken down biologically. One common technique for tracking a drug's fate is to label its molecular framework with heavier isotopes of hydrogen (either deuterium or tritium). Loh et al. developed a light-promoted protocol to install these labels on alkyl carbons adjacent to nitrogen. The technique relies on incorporation of the heavy isotope into a thiol from a convenient heavy water source through acid-base chemistry. Next, a photoredox catalyst strips a hydrogen atom equivalent from the carbon, and the thiol engages in radical chemistry to transfer the deuterium or tritium in its place. Science , this issue p. 1182