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Published on: January 16, 2016
Fluorous reagents and scavengers versus solid-supported reagents and scavengers, a reaction rate and kinetic
Christine Hiu-Tung Chen1, Wei Zhang
1Fluorous Technologies, Inc. University of Pittsburgh Applied Research Center, 970 William Pitt Way, Pittsburgh, PA 15238, USA.
Abstract:
Reactions using fluorous reagents and scavengers are compared side-by-side with their solid-supported counterparts. Fluorous triphenylphosphine is used in the bromination reaction of alcohols, fluorous thiol is used as an electrophile scavenger for alpha-bromoketones, fluorous isatoic anhydride is used as a nucleophile scavenger for primary and secondary amines. Reactions involving fluorous reagents and scavengers occur in homogeneous media with solution-phase reaction kinetics. Reactions with solid-supported reagents and scavengers occur in a heterogeneous media, and the reaction kinetics are greatly affected by the nature of the solid-support and reaction environment. Significantly larger amounts of reagents and more time are usually required to complete the solid-supported reaction.
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