A convenient method for the preparation of fluorous tin derivatives for the fluorous labeling strategy.
A convenient method for the preparation of fluorous aryl stannanes was developed as a means of expanding the general utility of the fluorous labeling strategy (FLS). Following the synthesis of a novel fluorous distannane, a palladium-catalyzed cross-coupling reaction was used to prepare the target compounds from aryl halides. The scope of the reaction was investigated by preparing a small library of model compounds where the reaction yields were similar to those reported for the analogous procedures employing hexamethyl- or hexabutyldistannanes. The utility of the reported methodology was demonstrated through the successful synthesis of fluorous precursors to two established molecular imaging and therapy agents (FIAU, IUdR). These were radiolabeled with iodine-125 and the desired products isolated in high yield and effective specific activity.
McIntee
Jason W
JW
Department of Chemistry, McMaster University, Hamilton, Ontario, Canada L8S 4M1.
Sundararajan
Chitra
C
Donovan
Amanda C
AC
Kovacs
Michael S
MS
Capretta
Alfredo
A
Valliant
John F
JF
D002384:Catalysis; D003432:Cross-Linking Reagents; D007457:Iodine Radioisotopes; D007553:Isotope Labeling / Q000379:methods*; D008722:Methods; D010165:Palladium; D014001:Tin / Q000737:chemistry*; D017971:Tin Compounds / Q000737:chemistry*
D003432:Cross-Linking Reagents; D007457:Iodine Radioisotopes; D017971:Tin Compounds; C031525:stannane; D010165:Palladium; D014001:Tin