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Article: Polytetrahydrofuran cross-linked polystyrene resins for solid-phase organic synthesis

TitlePolytetrahydrofuran cross-linked polystyrene resins for solid-phase organic synthesis
Authors
Issue Date2001
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jcc
Citation
Journal Of Combinatorial Chemistry, 2001, v. 3 n. 1, p. 117-124 How to Cite?
AbstractCurrently, divinylbenzene cross-linked polystyrene (DVB-PS) is the polymer of choice for use in solid-phase organic synthesis (SPOS). While much research has been directed toward the optimization of linker groups for the attachment of compounds to the polymer, the development of new polymers themselves has been relatively neglected. In an attempt to overcome the shortcomings of DVB-PS and to develop new polymers with optimum properties for use in organic synthesis, we have prepared a series of polystyrene polymers that incorporate flexible polytetrahydrofuran (PTHF) based cross-linkers. The objective of incorporating PTHF into the polymers was to slightly increase the overall polarity of the polymer and thus render the resins more organic solvent-like. Since the degree to which a resin swells in and absorbs a particular solvent correlates to how well substrates attached to the polymer are solvated, we compared the swelling of our new resins to commercially available DVB-PS resins. In all cases, we found that our resins swelled to a much greater extent than do DVB-PS resins, and their use should therefore allow for SPOS reaction conditions that more closely mimic homogeneous solution-phase conditions. It was also found that the PTHF chain length of the cross-linker does not affect the level of swelling since all of our cross-linkers afford resins with comparable levels of increased swelling. Furthermore, we have examined the utility of our resins in directed ortho-metalation reactions and found that the increased swelling of our resins allows for isolation of reaction products in yields comparable to what is achieved using standard solution-phase conditions.
Persistent Identifierhttp://hdl.handle.net/10722/167684
ISSN
2012 Impact Factor: 4.933
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorToy, PHen_US
dc.contributor.authorReger, TSen_US
dc.contributor.authorGaribay, Pen_US
dc.contributor.authorGarno, JCen_US
dc.contributor.authorMalikayil, JAen_US
dc.contributor.authorLiu, GYen_US
dc.contributor.authorJanda, KDen_US
dc.date.accessioned2012-10-08T03:10:00Z-
dc.date.available2012-10-08T03:10:00Z-
dc.date.issued2001en_US
dc.identifier.citationJournal Of Combinatorial Chemistry, 2001, v. 3 n. 1, p. 117-124en_US
dc.identifier.issn1520-4766en_US
dc.identifier.urihttp://hdl.handle.net/10722/167684-
dc.description.abstractCurrently, divinylbenzene cross-linked polystyrene (DVB-PS) is the polymer of choice for use in solid-phase organic synthesis (SPOS). While much research has been directed toward the optimization of linker groups for the attachment of compounds to the polymer, the development of new polymers themselves has been relatively neglected. In an attempt to overcome the shortcomings of DVB-PS and to develop new polymers with optimum properties for use in organic synthesis, we have prepared a series of polystyrene polymers that incorporate flexible polytetrahydrofuran (PTHF) based cross-linkers. The objective of incorporating PTHF into the polymers was to slightly increase the overall polarity of the polymer and thus render the resins more organic solvent-like. Since the degree to which a resin swells in and absorbs a particular solvent correlates to how well substrates attached to the polymer are solvated, we compared the swelling of our new resins to commercially available DVB-PS resins. In all cases, we found that our resins swelled to a much greater extent than do DVB-PS resins, and their use should therefore allow for SPOS reaction conditions that more closely mimic homogeneous solution-phase conditions. It was also found that the PTHF chain length of the cross-linker does not affect the level of swelling since all of our cross-linkers afford resins with comparable levels of increased swelling. Furthermore, we have examined the utility of our resins in directed ortho-metalation reactions and found that the increased swelling of our resins allows for isolation of reaction products in yields comparable to what is achieved using standard solution-phase conditions.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jccen_US
dc.relation.ispartofJournal of Combinatorial Chemistryen_US
dc.subject.meshCombinatorial Chemistry Techniquesen_US
dc.subject.meshCross-Linking Reagents - Chemistryen_US
dc.subject.meshFurans - Chemistryen_US
dc.subject.meshPolystyrenesen_US
dc.titlePolytetrahydrofuran cross-linked polystyrene resins for solid-phase organic synthesisen_US
dc.typeArticleen_US
dc.identifier.emailToy, PH:phtoy@hkucc.hku.hken_US
dc.identifier.authorityToy, PH=rp00791en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/cc000083fen_US
dc.identifier.pmid11148072en_US
dc.identifier.scopuseid_2-s2.0-0035228613en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0035228613&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume3en_US
dc.identifier.issue1en_US
dc.identifier.spage117en_US
dc.identifier.epage124en_US
dc.identifier.isiWOS:000167935000017-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridToy, PH=7006579247en_US
dc.identifier.scopusauthoridReger, TS=6601940573en_US
dc.identifier.scopusauthoridGaribay, P=7801588142en_US
dc.identifier.scopusauthoridGarno, JC=7004231697en_US
dc.identifier.scopusauthoridMalikayil, JA=6602873507en_US
dc.identifier.scopusauthoridLiu, GY=7501460097en_US
dc.identifier.scopusauthoridJanda, KD=35500092800en_US

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