Fluorous reagents and scavengers versus solid-supported reagents and scavengers, a reaction rate and kinetic comparison.
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.
Chen
Christine Hiu-Tung
CH
Fluorous Technologies, Inc. University of Pittsburgh Applied Research Center, 970 William Pitt Way, Pittsburgh, PA 15238, USA.
Zhang
Wei
W
D000588:Amines / Q000737:chemistry; D001592:Benzyl Alcohols / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D007202:Indicators and Reagents; D007659:Ketones; D007700:Kinetics; D009943:Organophosphorus Compounds; D010078:Oxazines; D010879:Piperazines; D013438:Sulfhydryl Compounds
C508280:2,4-dimethoxybenzyl alcohol; D000588:Amines; D001592:Benzyl Alcohols; D007202:Indicators and Reagents; D007659:Ketones; D009943:Organophosphorus Compounds; D010078:Oxazines; D010879:Piperazines; D013438:Sulfhydryl Compounds; C061896:triphenylphosphine; D005461:Fluorine; C031503:phenylpiperazine; C037902:isatoic anhydride