Multiple deuteration of triphenylphosphine and live-cell Raman imaging of deuterium-incorporated Mito-Q.

All aromatic C-H bonds of triphenylphosphine (PPh) were efficiently replaced by C-D bonds using Ru/C and Ir/C co-catalysts in 2-PrOH and DO, an inexpensive deuterium source. Furthermore, non-radioactive and safe deuterium-incorporated Mito-Q (drug candidate) was prepared from deuterated PPh and used for the live-cell Raman imaging to evaluate the mitochondrial uptake.