Stoichiometric and catalytic deuterium and tritium labeling of "unactivated" organic substrates with cationic Ir(III) complexes.
[reaction: see text] Ir(III) complex [Cp(PMe(3))IrMe(CH(2)Cl(2))][BAr(f)] (1) was used to introduce deuterium stoichiometrically into substituted naphthalene/benzene templates and several "drug-like" entities. The exchange process is tolerant of a wide array of functional groups. Labeling of warfarin using subatmospheric pressures of T(2) led to specific activities and total activities rivaling current functional group directed tritium labeling methods. When paired with the appropriate deuterium donor, Cp(PMe(3))Ir(H(3))OTf (4) was found to deuterate a number of organic compounds catalytically.
Skaddan
Marc B
MB
Pfizer Global Research and Development, Pfizer Inc., 301 Henrietta St., Kalamazoo, Michigan 49007, USA. marc.b.skadden@pfizer.com
Yung
Cathleen M
CM
Bergman
Robert G
RG