Fluorous Catalysis

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Science  16 Nov 2001:
Vol. 294, Issue 5546, pp. 1419-1421
DOI: 10.1126/science.294.5546.1419e

In fluorous biphasic catalysis, the catalysts are designed to be highly soluble in fluorous solvents. Reactions are usually run at high temperatures in a mixed organic-fluorous solvent that forms a single phase, and the catalysts are readily recovered at room temperature from the fluorous phase that separates from the organic solvent. The need for the highly fluorinated solvents has been seen in some circles as a critical drawback to this technique. Wende et al. now show that the fluorous solvent can be eliminated altogether in some cases by taking advantage of very large increases in solubility of the catalyst in organic solvents at temperatures at and above their melting points. For example, the addition of alcohols to the triple bond of methyl propiolate can be catalyzed by fluorous phosphines such as P((CH2)2(CF2)7CF3)3. These reactions can be run in octane at 65°C and the catalyst recovered as a solid at −30°C for further reaction cycles.—PDS

J. Am. Chem. Soc. 10.1021/ja011444d.

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