Main > ORGANIC CHEMICALS > HeteroCyclics > Hydantoin > Synthesis > Org.: FR. U. (Fluorous Chemistry) > Synthesis Description

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fluorous metal carboxylates. The team has used the compounds to develop a technique, known as reversible phase-switching, for separation and purification applications. The technique involves a "catch-and-release" strategy that relies on the reversible coordination of ligands with a nonfluorous tag to a fluorous-tagged metal carboxylate complex. Substrates or products coordinated with the nonfluorous ligands are soluble in a hydrocarbon organic phase. When the molecules with the nonfluorous tags are coordinated with the fluorous metal carboxylate, they become soluble in the fluorous phase. When a chelating solvent such as tetrahydrofuran (THF) is added, the nonfluorous-tagged substrates or products separate from the fluorous metal carboxylate and can be extracted into a hydrocarbon solvent.

Last year, the group showed that the technique can be applied to the preparation of hydantoin in high yield and purity using a nonfluorous pyridyl tag and a fluorous copper(II) carboxylate complex.

"Due to the high lability of the coordination bonds, release of the nonfluorous-tagged molecules into the hydrocarbon phase is achieved by simply adding THF in excess to the biphasic system." "The THF acts as a competitive ligand."




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