A Convenient Method for the Preparation of Fluorous Tin Derivatives for the Fluorous Labeling Strategy
- 1 October 2008
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 73 (21), 8236-8243
- https://doi.org/10.1021/jo8013287
Abstract
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.Keywords
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