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C-C Bond Formation Realized by Amidyl-Radical-Mediated Chain Reactions
C-C Bond Formation Realized by Amidyl-Radical-Mediated Chain Reactions
C-C Bond Formation Realized by Amidyl-Radical-Mediated Chain Reactions

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자료유형  
 학위논문 서양
최종처리일시  
20260202103116
ISBN  
9798315705246
DDC  
540
저자명  
Gruhin, Jonathan Nelson.
서명/저자  
C-C Bond Formation Realized by Amidyl-Radical-Mediated Chain Reactions
발행사항  
[Sl] : The University of North Carolina at Chapel Hill, 2025
발행사항  
Ann Arbor : ProQuest Dissertations & Theses, 2025
형태사항  
271 p
주기사항  
Source: Dissertations Abstracts International, Volume: 86-11, Section: B.
주기사항  
Advisor: Alexanian, Erik J.
학위논문주기  
Thesis (Ph.D.)--The University of North Carolina at Chapel Hill, 2025.
초록/해제  
요약I.X-H Functionalization as a Means for Achieving C-C Bond FormationAn overview of the benefits and challenges related to site-selective, intermolecular C(sp3)-H and carboxylic acid O-H functionalizations are discussed, particularly as they pertain to enabling C-C bond formation.II.Strategic Introduction of Carbon Fragments Onto Building Blocks and Late-Stage MoleculesThe development of an amidyl-radical-mediated chain reaction to convert aliphatic C(sp3)-H bonds into a variety of C-C bonds is discussed. The methods disclosed include (a) C-H functionalizations of tertiary alkylamines and (b) α-heteroatom C-H thioetherification followed by alkylation with an organometallic species.III. Decarboxylative Homologation Using a Radical-Polar Conjunctive Reagent The development of one-carbon homologation of aliphatic carboxylic acids is discussed. Particular attention is paid to the iterative design of a two-carbon SOMOphile that was critical to achieving the desired synthon for the overall transformation.IV.Rapid Access to Α-Ketoesters via C-H and Decarboxylative Pyruvylation Alpha-ketoesters are regarded as highly diversifiable intermediates in organic synthesis, with numerous applications ranging from unnatural amino acid construction to heterocycle formation. A late-stage approach to installing these functional handles onto C(sp3)-H and carboxylic acid-containing molecules is discussed.
일반주제명  
Chemistry
일반주제명  
Organic chemistry
키워드  
Aliphatic carboxylic acids
키워드  
Organometallic species
키워드  
Thioetherification
기타저자  
The University of North Carolina at Chapel Hill Chemistry
기본자료저록  
Dissertations Abstracts International. 86-11B.
전자적 위치 및 접속  
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■1001  ▼aGruhin,  Jonathan  Nelson.
■24510▼aC-C  Bond  Formation  Realized  by  Amidyl-Radical-Mediated  Chain  Reactions
■260    ▼a[Sl]▼bThe  University  of  North  Carolina  at  Chapel  Hill▼c2025
■260  1▼aAnn  Arbor▼bProQuest  Dissertations  &  Theses▼c2025
■300    ▼a271  p
■500    ▼aSource:  Dissertations  Abstracts  International,  Volume:  86-11,  Section:  B.
■500    ▼aAdvisor:  Alexanian,  Erik  J.
■5021  ▼aThesis  (Ph.D.)--The  University  of  North  Carolina  at  Chapel  Hill,  2025.
■520    ▼aI.X-H  Functionalization  as  a  Means  for  Achieving  C-C  Bond  FormationAn  overview  of  the  benefits  and  challenges  related  to  site-selective,  intermolecular  C(sp3)-H  and  carboxylic  acid  O-H  functionalizations  are  discussed,  particularly  as  they  pertain  to  enabling  C-C  bond  formation.II.Strategic  Introduction  of  Carbon  Fragments  Onto  Building  Blocks  and  Late-Stage  MoleculesThe  development  of  an  amidyl-radical-mediated  chain  reaction  to  convert  aliphatic  C(sp3)-H  bonds  into  a  variety  of  C-C  bonds  is  discussed.  The  methods  disclosed  include  (a)  C-H  functionalizations  of  tertiary  alkylamines  and  (b)  α-heteroatom  C-H  thioetherification  followed  by  alkylation  with  an  organometallic  species.III.  Decarboxylative  Homologation  Using  a  Radical-Polar  Conjunctive  Reagent  The  development  of  one-carbon  homologation  of  aliphatic  carboxylic  acids  is  discussed.  Particular  attention  is  paid  to  the  iterative  design  of  a  two-carbon  SOMOphile  that  was  critical  to  achieving  the  desired  synthon  for  the  overall  transformation.IV.Rapid  Access  to  Α-Ketoesters  via  C-H  and  Decarboxylative  Pyruvylation  Alpha-ketoesters  are  regarded  as  highly  diversifiable  intermediates  in  organic  synthesis,  with  numerous  applications  ranging  from  unnatural  amino  acid  construction  to  heterocycle  formation.  A  late-stage  approach  to  installing  these  functional  handles  onto  C(sp3)-H  and  carboxylic  acid-containing  molecules  is  discussed.
■590    ▼aSchool  code:  0153.
■650  4▼aChemistry
■650  4▼aOrganic  chemistry
■653    ▼aAliphatic  carboxylic  acids
■653    ▼aOrganometallic  species
■653    ▼aThioetherification
■690    ▼a0485
■690    ▼a0490
■71020▼aThe  University  of  North  Carolina  at  Chapel  Hill▼bChemistry.
■7730  ▼tDissertations  Abstracts  International▼g86-11B.
■790    ▼a0153
■791    ▼aPh.D.
■792    ▼a2025
■793    ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17357010▼nKERIS▼z이  자료의  원문은  한국교육학술정보원에서  제공합니다.

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