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Transition metal catalysis for organic synthesis

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Text
TitleInfo (ID = T-1)
Title
Transition metal catalysis for organic synthesis
SubTitle
PartName
PartNumber
NonSort
Identifier (displayLabel = ); (invalid = )
ETD_2122
Identifier (type = hdl)
http://hdl.rutgers.edu/1782.2/rucore10001600001.ETD.000051912
Language (objectPart = )
LanguageTerm (authority = ISO639-2); (type = )
eng
Genre (authority = marcgt)
theses
Subject (ID = SBJ-1); (authority = RUETD)
Topic
Chemistry and Chemical Biology
Subject (ID = SBJ-2); (authority = ETD-LCSH)
Topic
Transition metal catalysis
Subject (ID = SBJ-3); (authority = ETD-LCSH)
Topic
Organic compounds--Synthesis
Abstract
Transition metal-catalyzed reactions are one of the most powerful and direct approaches for the synthesis of organic molecules. During the past several decades, phosphorus containing ligands have been extensively used in transition metal catalyzed C-C and C-H bond forming reactions. Development of new phosphine ligands for palladium cross coupling and also methodology for C-H activation strategies will be the focus of this dissertation. A variety of triazole containing
monophosphine ligands have been prepared via efficient 1,3-dipolar cycloaddition of readily available azides and acetylenes. Their palladium complexes provided excellent yields in the amination reactions (up to 98% yield) and Suzuki-Miyaura coupling reactions (up to 99% yield) of unactivated aryl chlorides. A CAChe model for one of the Pd-complexes shows that the likelihood of a Pd-arene interaction might be a rationale for its high catalytic reactivity. A main goal for Organic chemists is to develop and utilize efficient and atom-economical methods for the elaboration of complex structures from simple and readily available starting materials. C-H bonds are the most fundamental linkage in organic chemistry and recently tremendous strides have been have been made in the functionalization of C-H bonds. A central goal in the development of any new methodology is synthetic utility, which has been difficult to achieve with C-H activation strategies because of the inherent stability of C-H bond. Aryl carboxylic acid derivatives are very prevalent in industrial and pharmaceuticals and thus a direct C-H activation approach would be very desirable. A general protocol for the rhodium-catalyzed oxidative carbonylation of arenes to form esters has been developed. A broad substrate scope has been demonstrated allowing carbonylation of electron rich, electron-poor, and heterocyclic arenes, and the reaction shows wide functional group tolerance and excellent regioselectivities. Up to 96% yield of ortho-substituted aryl or heteroaryl carboxylic esters were obtained with this methodology. The possible mechanism for the rhodium-catalyzed oxidative carbonylation reaction was proposed in this article. Studies show that Oxone play an important role in the transformation. We have developed a new C2-symmetric monophosphine ligand based upon a C3* tunephos backbone. The ligand was available in several steps from commercially available starting materials. In future studies this ligand was be tested for its use in chiral cross coupling reactions.
PhysicalDescription
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electronic resource
Extent
viii, 57 p. : ill.
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application/pdf
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text/xml
Note (type = degree)
M.S.
Note (type = bibliography)
Includes bibliographical references
Note (type = statement of responsibility)
by Stephen Spinella
Name (ID = NAME-1); (type = personal)
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Spinella
NamePart (type = given)
Stephen
NamePart (type = date)
1984-
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author
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Stephen Spinella
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Zhang
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Xumu
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chair
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Advisory Committee
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Xumu Zhang
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Goldman
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Alan
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internal member
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Advisory Committee
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Alan S Goldman
Name (ID = NAME-4); (type = personal)
NamePart (type = family)
Romsted
NamePart (type = given)
Laurence
Role
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internal member
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Advisory Committee
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Laurence S Romsted
Name (ID = NAME-1); (type = corporate)
NamePart
Rutgers University
Role
RoleTerm (authority = RULIB); (type = )
degree grantor
Name (ID = NAME-2); (type = corporate)
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Graduate School - New Brunswick
Role
RoleTerm (authority = RULIB); (type = )
school
OriginInfo
DateCreated (point = ); (qualifier = exact)
2009
DateOther (qualifier = exact); (type = degree)
2009-10
Place
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xx
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Title
Rutgers University Electronic Theses and Dissertations
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ETD
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Title
Graduate School - New Brunswick Electronic Theses and Dissertations
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rucore19991600001
Location
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NjNbRU
Identifier (type = doi)
doi:10.7282/T3CC10VW
Genre (authority = ExL-Esploro)
ETD graduate
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The author owns the copyright to this work
Copyright
Status
Copyright protected
Notice
Note
Availability
Status
Open
Reason
Permission or license
Note
RightsHolder (ID = PRH-1); (type = personal)
Name
FamilyName
Spinella
GivenName
Stephen
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Copyright holder
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DateTime
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Name
Stephen Spinella
Affiliation
Rutgers University. Graduate School - New Brunswick
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License
Name
Author Agreement License
Detail
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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