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.
Studer
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A
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
Hadida
S
S
Ferritto
R
R
Kim
S Y
SY
Jeger
P
P
Wipf
P
P
Curran
D P
DP
D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D003514:Cyclohexylamines / Q000138:chemical synthesis* / Q000737:chemistry; D005466:Fluorocarbons / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility; D012997:Solvents
C103917:2-(5-ethoxycarbonyl-4-ethyl-6-(2-naphthyl)-1,2,3,6-tetrahydro-2-oxopyrimidin-1-yl)ethyl benzoate; D001549:Benzamides; D001565:Benzoates; D003514:Cyclohexylamines; D005466:Fluorocarbons; C103916:N-benzyl-N-(1-cyclohexyl-2-cyclohexylamino-2-oxoethyl)benzamide; D009570:Nitriles; D011744:Pyrimidinones; D012997:Solvents