Fluorous synthesis: A fluorous-phase strategy for improving separation efficiency in organic synthesis

Recovery and purification difficulties can limit the yield and utility of otherwise successful organic synthesis strategies. A ''fluorous synthesis'' approach is outlined in which organic molecules are rendered soluble in fluorocarbon solvents by attachment of a suitable fluorocarbon group. Fluorocarbon solvents are usually immiscible in organic solutions, and fluorous molecules partition out of an organic phase and into a fluorous phase in a standard liquid-liquid extraction. Simple yet substantive separations of organic reaction mixtures are achieved without resorting to chromatography. Because fluorous synthesis combines in many respects the favorable purification features of solid-phase synthesis with the favorable reaction, identification, and analysis features of traditional organic synthesis,it should prove valuable in the automated synthesis of libraries of individual pure organic compounds.