Regioselective catalytic deuteriation of phospholipids—unusual mechanistic aspects of homogeneous hydrogenation

Abstract

Reaction of unsaturated phospholipids, R¹HCCHR², with D₂ in aqueous (H₂O) dispersions with Pd^II–alizarin red as the catalyst results in formation of R¹H₂C–CD₂R²(in addition to the expected R¹HDC–CDHR²); however, only the latter is formed with H₂ in D₂O, which reveals the importance of the reversible formation of an intermediate alkylmetal species.