Fluorous technology

Microwave and fluorous technologies have been combined in the solution phase parallel synthesis of 3-aminoimidazo[l,2-a]pyridines and -pyrazines [63]. The three-component condensation of a perfluorooctane-sulfonyl (Rfs = CgFiy) substituted benzaldehyde by microwave irradiation in a single-mode instrument at 150 °C for 10 min in CH2CI2 - MeOH in the presence of Sc(OTf)3 gave the imidazo-annulated heterocycles that could be purified by fluorous solid phase extraction (Scheme 9). Subsequent Pd-catalyzed cross-coupling reactions of the fluorous sulfonates with arylboronic acids or thiols gave biaryls or aryl sulfides, respectively, albeit it in relatively low yields. 

Fluorous Technologies Bulletin on Fluorous Scavenging, www.fluorous.com/html. 

Lantos D, Contel M, Sanz S, Horvdth IT (2005) In Book of abstracts, 1st international symposium on fluorous technologies, Bordeaux, 3-6 July 2005... 

Fluorous Technologies, Inc., University of Pittsburgh Applied Research Center,... 

Compound library synthesis relies heavily on integrated technologies to address both reaction and separation issues. The good combinatorial capability of the fluorous technology has demonstrated its great potential in this area [9]. 

The integration of microwave heating and fluorous technologies has generated a powerful solution to address both the reaction and separation issues in parallel and combinatorial synthesis. With the further development of multimode microwave reactors for plate reactions and F-SPE for plate-to-plate separations, microwave-assisted fluorous synthesis will play an even more important role in compound library synthesis. 

C4F9C2H4), are highly fluorophilic and exhibit large partition coefficients in favor of fluorocarbon solvents over common organic solvents due to a double-layered structure where the stannoxane core is covered by fluoroalkyl groups. Fluorous technology allows transesterification and esterification in which 100% yield of the desired esters is achievable with reactants in a strict 1 1 ratio. The tin catalysts are recovered from the fluorous phase quantitatively (Equation (95)).260... 

Zhang, W. 2003. Fluorous technologies for solution-phase high-throughput organic synthesis. 

The basic idea of fluorous technology stems from the facile separation of organic products and fluorous catalysts, staying in the organic and fluorous phases, respectively, owing to incompatibility of the two reaction media.The catalysts can be easily recovered from the fluorous phase, or preferably the fluorous solution can be used repeatedly without isolating the catalysts. It is reasonable to assume that such unique solubility characteristics might be reflected in the equilibration as well. Based on this simple expectation, fluorous biphasic (trans)esteriflcation has been pursued by use of fluorous distannoxane catalysts. 

Fluorous technologies for reactions with participation of A-heterocycles 03T4475. 

Fluoroflash fluorous silica gel cartridges are available from Fluorous Technologies, Inc www.fluorous.com... 

Zhang and Tempest have efficiently incorporated microwave and fluorous technologies m a Ugi-de-Boc cyclization strategy for construction of qurnoxalinones and... 

Fluorous solid-phase extractions are readily conducted in parallel (or serial), with or without automation. All reaction mixtures are processed identically and behave in substantially the same way, even though all the products are different. Careful fractionation and analysis are not required there is one organic fraction and one fluorous fraction. Because the separation is so easy, loading levels can be high. Loose fluorous silica gel and cartridges suitable for solid-phase extraction have recently been commercialized under the trademark FluoroF/dj/i by Fluorous Technologies, Inc. ... 

Synthesis of 2H,2H,3H,3H-Perfluoro-uiidecaiioic-acid-N-succinimidyl-ester. 2H,2H,3H, 3H-PerfIuoroundecanoic acid (1.354 g, 2.75 mmol, Fluorous Technologies Inc., Pittsburgh, PA), A-hydroxysuccinimide (348 mg, 3.02 mmol), and dicyclo-hexylcarbodiimide (622 mg, 3.02 mmol) were dissolved in ethyl acetate (120 mL) and stirred for 18 h at room temperature. The white precipitate formed (dicyclohexyl urea, DCU) was filtered off, and the remaining solution evaporated to dryness. The residue was recrystallized twice from ethyl acetate. Yield 1.00 g (62%), containing some traces of DCU. NMR (CDCI3, 300 MHz, ppm) 3.0 (m, 2H CH2), 2.88 (s, 4H CH2 NHS), 2.6 (m, 2H CH2). 

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