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Permanent link (DOI): https://doi.org/10.7939/R3SP7J

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Reusable Ru and Rh catalysts for ester hydrogenations and enyne cycloisomerizations Open Access

Descriptions

Other title
Subject/Keyword
cycloisomerization
rhodium
catalyst immobilization
catalysis
enantioselective
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Hass, Michael J.
Supervisor and department
Bergens, Steven H. (Chemistry)
Examining committee member and department
Buriak, Jillian M. (Chemistry)
Semagina, Natalia (Chemical and Materials Engineering)
Bergens, Steven H. (Chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2012-05-30T16:01:09Z
Graduation date
2011-06
Degree
Master of Science
Degree level
Master's
Abstract
A method was developed to immobilize and reuse a catalyst for the asymmetric cycloisomerization of enynes. Immobilization is achieved through use of metal containing monomers, which are reacted with a cycloolefin via an alternating ring-opening metathesis polymerization, assembling a three-dimensional catalyst-organic framework. For example, [RhCl((R)-5,5'-dinorimido BINAP)]2 was copolymerized with ciscyclooctene using trans-RuCl2(CHPh)(PCy3)2 as a catalyst. After supporting the resulting framework on barium sulphate, silver(I) hexafluoroantimonate was added in the presence of enyne substrates to generate cationic rhodium(I) sites. These catalytic rhodium(I) sites catalyzed the asymmetric cycloisomerization of enynes, and afforded a maximum of 620 turnovers and >99% ee over the course of six runs. This catalyst was also used for batch reactions with turnovers as high as 800. The maximum number of turnovers reported in literature for a homogeneous non-tandem cycloisomerization reaction is ten.
Language
English
DOI
doi:10.7939/R3SP7J
Rights
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
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File title: MHass Thesis Together
File author: Michael Hass
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