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1 2009

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Reaktywne żywice polimerowe do szybkiego oczyszczania produktów reakcji

Bukowska A., Bukowski W.

Wiadomości Chemiczne

2009

[Z] 63, 11-12

10031047-10031047

One of the major drawbacks of solution phase organic synthesis is laborious processes of purification and isolation of individual products. Problems intensify in the case of preparation of compound libraries for pharmaceutical and agrochemical research. Application of oligomeric or polymeric specific reagents in purification processes can simplify significantly the isolation of organic products. Techniques of purification with reactive polymers have been worked out in the mid-1990s independently by groups of Kaldor, Flynn and Hodge as solid phase scavenging, complementary molecular reactivity and molecular recognition (CMR/R) or polymersupported quench (PSQ), respectively [55–58]. They are based on differences in the reactivity of impurities in comparison to desired products with reference to functional groups of polymers. The methodologies have been intensively developed for the last decade as an effective alternative to time-consuming and somehow difficult classical methods of purification such as extraction in water-organic solvent systems, chromatography, crystallization or distillation [23, 25]. As a result of that, many new scavenging resins were synthesized and commercialized [51–54]. Their application seems to be particularly useful for purification of products from combinatorial synthesis. The synthesis of libraries of amides, carbamides, sulfoamides or amines can be taken as examples. The methods are also useful in many cases when classical methods of purification do not give desired effects. Removing of metal ions impurities from pharmaceutical products can be a good example [109]. The effectiveness of purification by reactive polymers was proven both in the case of single reactions and multi-step transformations. In this review the basic principles of using functionalized polymers in purification of organic reaction products were described. The division of scavenging resins depending on the chemical nature of functional group immobilized on polymers and their applications was performed. Methods of synthesis of different types of oligomeric and polymeric scavengers and their morphology were discussed. Numerous examples of practical applications of scavenging resins in modern organic synthesis were presented.