Recyclable palladium(0)-catalyzed addition of silylstannanes to terminal alkynes in ionic liquids

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dc.contributor.advisor Singer, Robert D. (Robert Douglas), 1964-
dc.creator Hemeon, Ivan W.
dc.date.accessioned 2011-05-09T12:32:15Z
dc.date.available 2011-05-09T12:32:15Z
dc.date.issued 2003
dc.identifier.other QD562 I65 H46 2003
dc.identifier.uri http://library2.smu.ca/xmlui/handle/01/22528
dc.description x, 109 leaves : ill. ; 28 cm.
dc.description Includes abstract.
dc.description Includes bibliographical references (leaves 104-109).
dc.description.abstract Ionic liquids have been used as solvents for many different organic reactions, often providing rate enhancements, selectivity improvements, and affording better yields compared to conventional solvents. In this study, the palladium(0)-catalyzed addition of trimethyl(tributylstannyl)silane and diphenylmethyl(tributylstannyl)silane to terminal alkynes is investigated using two different ionic liquids, 1- n -butyl-3-methylimidazolium hexafluorophosphate and 1- n -butyl-3-methylimidazolium tetrafluoroborate, under biphasic conditions using diethyl ether as a co-solvent. Five terminal alkynes were used, phenylacetylene, 1-decyne, 5-hexyn-1-ol, 5-hexyn-1-ol THP ether, and 6-chlorohexyne. In general, reactions between the silylstannanes and alkynes proceeded efficiently in both ionic liquids to give quantitative or near quantitative yields of their addition products as a single isomer. Ionic liquids have gained much popularity of late due to their ability to immobilize transition metal catalysts, allowing them to be recycled due to the nonvolatile nature of ionic liquids. The tetrakis(triphenylphosphine)palladium(0) catalyst used in these silylstannation reactions was immobilized in both ionic liquids and shown to be extensively recyclable without loss of activity. Ionic liquid/catalyst systems were recycled ten times in the reaction of phenylacetylene with trimethyl(tributylstannyl)silane.
dc.language.iso en
dc.publisher Halifax, N.S. : Saint Mary's University
dc.subject.lcc QD562.I65
dc.subject.lcsh Ionic solutions
dc.subject.lcsh Solvents
dc.subject.lcsh Alkynes
dc.title Recyclable palladium(0)-catalyzed addition of silylstannanes to terminal alkynes in ionic liquids
dc.type Text
thesis.degree.name Master of Science in Applied Science
thesis.degree.level Masters
thesis.degree.discipline Chemistry
thesis.degree.grantor Saint Mary's University (Halifax, N.S.)


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