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Catalytic C-C (C-N) bond formation and C-O bond cleavage by pincer-ligated iridium complexes

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Title
Catalytic C-C (C-N) bond formation and C-O bond cleavage by pincer-ligated iridium complexes
Name (type = personal)
NamePart (type = family)
Li
NamePart (type = given)
Bo
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Bo Li
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author
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Goldman
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Alan S.
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Alan S. Goldman
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Advisory Committee
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chair
Name (type = personal)
NamePart (type = family)
Celik
NamePart (type = given)
Fuat E.
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Fuat E. Celik
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Advisory Committee
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internal member
Name (type = personal)
NamePart (type = family)
Lipke
NamePart (type = given)
Mark
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Mark Lipke
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Advisory Committee
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internal member
Name (type = personal)
NamePart (type = family)
Prokopchuk
NamePart (type = given)
Demyan
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Demyan Prokopchuk
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Advisory Committee
Role
RoleTerm (authority = RULIB)
outside member
Name (type = corporate)
NamePart
Rutgers University
Role
RoleTerm (authority = RULIB)
degree grantor
Name (type = corporate)
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School of Graduate Studies
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school
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Text
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theses
OriginInfo
DateCreated (encoding = w3cdtf); (keyDate = yes); (qualifier = exact)
2019
DateOther (encoding = w3cdtf); (qualifier = exact); (type = degree)
2019-05
Language
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English
Abstract (type = abstract)
Since the initial reports of catalytic alkane dehydrogenation by (tBuPCP)Ir (tBuPCP = κ3-2,6-C6H3(CH2tBu2)2) in 1996, pincer-iridium complexes have grown rapidly to include a family of derivatives. No longer limited to the original application of dehydrogenation, this new growing family shows versatile applications such as activation of X-H (X = C, N, O, Si) bonds, tandem dehydrogenation/olefin-metathesis, activation of other strong bonds, catalytic phenol-type C-O bond formation and cleavage. However, there are surprisingly few examples of dehydrogenative couplings of C−H bonds catalyzed by pincer-iridium complex, though it shows to be the ideal route for C-C bond formation. The substrates for catalytic C-O bond cleavage were also limited to alkyl phenol ethers. My PhD dissertation research aimed to discover and elucidate the mechanisms of a wider range of C-C (C-N) bond formation and C-O cleavage reactions catalyzed by pincer-ligated iridium complexes.
Chapter 2 presents the development of a tandem catalytic system for aryl-alkyl coupling. Iridium pincer complexes together with zeolites are used to convert pentylbenzene to methylnaphthalene, with hydrogen gas as the only byproduct. The utility of this method is demonstrated in the preparation of 2,6-dimethylnaphthalene, a feedstock for high performance polyesters.
Chapter 3, 4 and 5 describes the development and mechanistic investigation of dehydrogenative coupling reactions. Diaryl butadienes are obtained by homo-coupling. Cross-dehydrogenative coupling vinyl arenes with furan, thiophene, aromatics, and olefins is also demonstrated. A metalloindene complex is shown to be the key intermediate in these reactions. An intramolecular dehydrogenative coupling for the synthesis of indene and indole from vinyl arene and vinyl aniline, respectively, is further shown.
In Chapter 6, the catalytic hydrogenolysis of C-O bonds by pincer iridium complexes is shown. 1,3-diols and triols are partially deoxygenated under H2 atmosphere. An important application for this reaction is illustrated by the high yielding conversion of glycerol, an abundant side product from biofuel production, to 1,2-propanediol, a useful solvent and chemical intermediate.
Lastly, I synthesized a new pincer-iridium complex (iPrNCOP)Ir and utilized it for C-C bond formation and C-O bond cleavage.
Subject (authority = RUETD)
Topic
Chemistry and Chemical Biology
Subject (authority = local)
Topic
C-C bond formation
Subject (authority = local)
Topic
C-O bond cleavage
Subject (authority = local)
Topic
Dehydrogenation
Subject (authority = local)
Topic
Dehydrogenative coupling
Subject (authority = local)
Topic
Hydrogenolysis
Subject (authority = local)
Topic
Pincer-ligated iridium complex
RelatedItem (type = host)
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Title
Rutgers University Electronic Theses and Dissertations
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ETD_9837
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application/pdf
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text/xml
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1 online resource (xxx, 388 pages) : illustrations
Note (type = degree)
Ph.D.
Note (type = bibliography)
Includes bibliographical references
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School of Graduate Studies Electronic Theses and Dissertations
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rucore10001600001
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Identifier (type = doi)
doi:10.7282/t3-zw50-rh23
Genre (authority = ExL-Esploro)
ETD doctoral
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The author owns the copyright to this work.
RightsHolder (type = personal)
Name
FamilyName
Li
GivenName
Bo
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Copyright Holder
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Type
Permission or license
DateTime (encoding = w3cdtf); (qualifier = exact); (point = start)
2019-04-12 12:06:21
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Bo Li
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Rutgers University. School of Graduate Studies
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I hereby grant to the Rutgers University Libraries and to my school the non-exclusive right to archive, reproduce and distribute my thesis or dissertation, in whole or in part, and/or my abstract, in whole or in part, in and from an electronic format, subject to the release date subsequently stipulated in this submittal form and approved by my school. I represent and stipulate that the thesis or dissertation and its abstract are my original work, that they do not infringe or violate any rights of others, and that I make these grants as the sole owner of the rights to my thesis or dissertation and its abstract. I represent that I have obtained written permissions, when necessary, from the owner(s) of each third party copyrighted matter to be included in my thesis or dissertation and will supply copies of such upon request by my school. I acknowledge that RU ETD and my school will not distribute my thesis or dissertation or its abstract if, in their reasonable judgment, they believe all such rights have not been secured. I acknowledge that I retain ownership rights to the copyright of my work. I also retain the right to use all or part of this thesis or dissertation in future works, such as articles or books.
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