Staff View
Cross-coupling of amides by N-C bond activation

Descriptive

TitleInfo
Title
Cross-coupling of amides by N-C bond activation
Name (type = personal)
NamePart (type = family)
Meng
NamePart (type = given)
Guangrong
NamePart (type = date)
1987-
DisplayForm
Guangrong Meng
Role
RoleTerm (authority = RULIB)
author
Name (type = personal)
NamePart (type = family)
Szostak
NamePart (type = given)
Michal
DisplayForm
Michal Szostak
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
chair
Name (type = personal)
NamePart (type = family)
He
NamePart (type = given)
Huixin
DisplayForm
Huixin He
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Sheridan
NamePart (type = given)
John
DisplayForm
John Sheridan
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Lakshman
NamePart (type = given)
Mahesh
DisplayForm
Mahesh Lakshman
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
outside member
Name (type = corporate)
NamePart
Rutgers University
Role
RoleTerm (authority = RULIB)
degree grantor
Name (type = corporate)
NamePart
Graduate School - Newark
Role
RoleTerm (authority = RULIB)
school
TypeOfResource
Text
Genre (authority = marcgt)
theses
OriginInfo
DateCreated (encoding = w3cdtf); (qualifier = exact)
2019
DateOther (encoding = w3cdtf); (qualifier = exact); (type = degree)
2019-10
CopyrightDate (encoding = w3cdtf); (qualifier = exact)
2019
Language
LanguageTerm (authority = ISO 639-3:2007); (type = text)
English
Abstract (type = abstract)
The amide bond is one the most important functional motifs in chemistry and biology. However, despite the central role of amides as ubiquitous pharmacophores in medicinal chemistry, but also as bench-stable intermediates in organic synthesis, transition-metal- catalyzed transformations of amides by N-C bond activation have been unexplored. The major reason is that high activation energy is required for the N-C(O) bond scission due to n<sub>N→*πC=O</sub> conjugation (amide bond resonance of 15-20 kcal/mol in planar amides, ca. 40% double bond character). In 2015, we introduced a new generic mode of activation of amide bonds by geometric distortion, whereby metal insertion into an inert amide bond can proceed only if the classic Pauling's amide bond resonance has been disrupted. With this new concept put forward, we successfully developed several new types of twisted amides and metal-catalyzed transformations during my Ph.D. research.
The focus of this thesis is on three parts: (1) the use of amides as acyl electrophiles in metal-catalyzed Suzuki cross-coupling reactions; (2) the use of amides as aryl electrophiles in metal-catalyzed cross-coupling reactions, including palladium-catalyzed Heck reaction and rhodium-catalyzed C-H bond functionalization; (3) the development of new type of amides as acyl electrophiles with the use of new Pd-NHC catalyst systems. These studies have demonstrated the potential of amides as acyl- and aryl-electrophiles in catalytic cross-coupling chemistry by activation of the typically inert amide N-C(O) bond.
Subject (authority = RUETD)
Topic
Chemistry
Subject (authority = local)
Topic
Twisted amides
Subject (authority = LCSH)
Topic
Amides -- Electric properties
RelatedItem (type = host)
TitleInfo
Title
Rutgers University Electronic Theses and Dissertations
Identifier (type = RULIB)
ETD
Identifier
ETD_10086
PhysicalDescription
Form (authority = gmd)
InternetMediaType
application/pdf
InternetMediaType
text/xml
Extent
1 online resource (xviii, 275 pages) : illustrations
Note (type = degree)
Ph.D.
Note (type = bibliography)
Includes bibliographical references
RelatedItem (type = host)
TitleInfo
Title
Graduate School - Newark Electronic Theses and Dissertations
Identifier (type = local)
rucore10002600001
Location
PhysicalLocation (authority = marcorg); (displayLabel = Rutgers, The State University of New Jersey)
NjNbRU
Identifier (type = doi)
doi:10.7282/t3-agys-a942
Genre (authority = ExL-Esploro)
ETD doctoral
Back to the top

Rights

RightsDeclaration (ID = rulibRdec0006)
The author owns the copyright to this work.
RightsHolder (type = personal)
Name
FamilyName
Meng
GivenName
Guangrong
Role
Copyright Holder
RightsEvent
Type
Permission or license
DateTime (encoding = w3cdtf); (qualifier = exact); (point = start)
2019-06-20 17:54:39
AssociatedEntity
Name
Guangrong Meng
Role
Copyright holder
Affiliation
Rutgers University. Graduate School - Newark
AssociatedObject
Type
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.
RightsEvent
Type
Embargo
DateTime (encoding = w3cdtf); (qualifier = exact); (point = start)
2019-10-31
DateTime (encoding = w3cdtf); (qualifier = exact); (point = end)
2021-10-30
Detail
Access to this PDF has been restricted at the author's request. It will be publicly available after October 30th, 2021.
Copyright
Status
Copyright protected
Availability
Status
Open
Reason
Permission or license
Back to the top

Technical

RULTechMD (ID = TECHNICAL1)
ContentModel
ETD
OperatingSystem (VERSION = 5.1)
windows xp
CreatingApplication
Version
1.7
ApplicationName
Microsoft® Word for Office 365
DateCreated (point = end); (encoding = w3cdtf); (qualifier = exact)
2019-07-01T04:37:18
DateCreated (point = end); (encoding = w3cdtf); (qualifier = exact)
2019-07-01T04:37:18
Back to the top
Version 8.5.5
Rutgers University Libraries - Copyright ©2024