Application of Silicon-Based Cross-Coupling Technology to Aryl Triflates

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dc.contributor.advisorDeShong, Philipen_US
dc.contributor.authorRiggleman, Shaundraen_US
dc.contributor.departmentChemistryen_US
dc.date.accessioned2004-06-04T05:41:40Z
dc.date.available2004-06-04T05:41:40Z
dc.date.issued2004-05-06en_US
dc.description.abstractThe goal of this research was to explore the use of aryl silatranes as a replacement for aryl siloxanes in the palladium-catalyzed cross-coupling reaction with aryl triflates. Phenylsilatrane underwent fluoride-induced cross-coupling with aryl triflates to provide unsymmetrical biaryl derivatives in good to excellent yields. Typically, better yields of adduct were obtained for aryl triflates bearing electron-donating substituents than electron withdrawing substituents. Optimization of cross-coupling reaction revealed that addition of small amounts of water, the Denmark modification, dramatically improved reaction yields. Phenylsilatrane was found also to cross-couple in good to excellent yields with aryl halides having either electron-donating or electron-withdrawing substituents, although the yields of biaryl are lower than with the corresponding siloxane derivatives. Aryl siloxanes that had previously failed to couple with aryl triflates can be employed for triflate couplings using the Denmark modification although the yields of biaryls are generally lower than the corresponding silatrane reactions.en_US
dc.format.extent412325 bytes
dc.format.mimetypeapplication/pdf
dc.identifier.urihttp://hdl.handle.net/1903/1444
dc.language.isoen_US
dc.relation.isAvailableAtDigital Repository at the University of Marylanden_US
dc.relation.isAvailableAtUniversity of Maryland (College Park, Md.)en_US
dc.subject.pqcontrolledChemistry, Organicen_US
dc.subject.pquncontrolledSilatraneen_US
dc.subject.pquncontrolledAlcoholysis of Aryl Triflatesen_US
dc.subject.pquncontrolledPalladium mediated cross-coupling of aryl silatranesen_US
dc.titleApplication of Silicon-Based Cross-Coupling Technology to Aryl Triflatesen_US
dc.typeThesisen_US

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