Fluorous synthesis of allylic fluorides: C-F bond formation as the detagging process

摘要

A novel fluorous tagging-detagging strategy has been developed featuring a fluorination as the detagging process; fluorous allvlsilanes were prepared by cross-metathesis and subsequently subjected to electrophilic fluorodesilylation; Selectfluor was used as the detagging reagent; the resulting allylic fluorides were successfully purified by fluorous solid phase extraction. The ability of fluorine to alter the physical and chemical properties of organic molecules has been used in the design of fluorine-containing bioactive compounds.' Rapid and efficient protocols for the purification of fluorinated compounds are therefore in high demand. Radiochemists working in the area of positron emission tomography would also greatly benefit from the availability of fast purification strategies for the production of short half-life fluorinated ~(18)F-radiotracers.