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Deaminative Functionalizations of Primary Amines Enabled by Photoredox Catalysis
Deaminative Functionalizations of Primary Amines Enabled by Photoredox Catalysis
Deaminative Functionalizations of Primary Amines Enabled by Photoredox Catalysis

상세정보

자료유형  
 학위논문 서양
최종처리일시  
20250211152022
ISBN  
9798383163795
DDC  
547
저자명  
Dorsheimer, Julia R.
서명/저자  
Deaminative Functionalizations of Primary Amines Enabled by Photoredox Catalysis
발행사항  
[Sl] : Columbia University, 2024
발행사항  
Ann Arbor : ProQuest Dissertations & Theses, 2024
형태사항  
318 p
주기사항  
Source: Dissertations Abstracts International, Volume: 85-12, Section: B.
주기사항  
Advisor: Rovis, Tomislav.
학위논문주기  
Thesis (Ph.D.)--Columbia University, 2024.
초록/해제  
요약Utilizing primary amines as alkyl coupling partners has garnered attention in recent years due to their widespread availability, facile preparation and purification, and presence in a variety of common building blocks. The reemergence of Katritzky salts has enabled deaminative alkylation and arylation of α-1° and α-2° amines. The Rovis group has developed deaminative conditions for α-3° amines utilizing redox-active imines to generate tertiary carbon-centered radicals. Herein, we couple this tertiary alkyl radical to haloarenes to generate benzylic quaternary centers, a common motif in pharmaceuticals and natural products. We then applied this methodology in the realm of isotopic exchange to generate 15N-primary amines from their naturally occurring 14N-analogues. By activating α-1° and α-2° amines to Katritzky pyridinium salts and α−3° amines to redox-active imines, we can engage primary alkyl amines in a late-stage isotopic exchange with complete and selective isotopic labelling.
일반주제명  
Organic chemistry
일반주제명  
Chemistry
키워드  
Deaminative alkylation
키워드  
Alkyl amines
키워드  
Photoredox catalysis
기타저자  
Columbia University Chemistry
기본자료저록  
Dissertations Abstracts International. 85-12B.
전자적 위치 및 접속  
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MARC

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■035    ▼a(MiAaPQ)AAI31332422
■040    ▼aMiAaPQ▼cMiAaPQ
■0820  ▼a547
■1001  ▼aDorsheimer,  Julia  R.
■24510▼aDeaminative  Functionalizations  of  Primary  Amines  Enabled  by  Photoredox  Catalysis
■260    ▼a[Sl]▼bColumbia  University▼c2024
■260  1▼aAnn  Arbor▼bProQuest  Dissertations  &  Theses▼c2024
■300    ▼a318  p
■500    ▼aSource:  Dissertations  Abstracts  International,  Volume:  85-12,  Section:  B.
■500    ▼aAdvisor:  Rovis,  Tomislav.
■5021  ▼aThesis  (Ph.D.)--Columbia  University,  2024.
■520    ▼aUtilizing  primary  amines  as  alkyl  coupling  partners  has  garnered  attention  in  recent  years  due  to  their  widespread  availability,  facile  preparation  and  purification,  and  presence  in  a  variety  of  common  building  blocks.  The  reemergence  of  Katritzky  salts  has  enabled  deaminative  alkylation  and  arylation  of  α-1°  and  α-2°  amines.  The  Rovis  group  has  developed  deaminative  conditions  for  α-3°  amines  utilizing  redox-active  imines  to  generate  tertiary  carbon-centered  radicals.  Herein,  we  couple  this  tertiary  alkyl  radical  to  haloarenes  to  generate  benzylic  quaternary  centers,  a  common  motif  in  pharmaceuticals  and  natural  products.  We  then  applied  this  methodology  in  the  realm  of  isotopic  exchange  to  generate  15N-primary  amines  from  their  naturally  occurring  14N-analogues.  By  activating  α-1°  and  α-2°  amines  to  Katritzky  pyridinium  salts  and  α−3°  amines  to  redox-active  imines,  we  can  engage  primary  alkyl  amines  in  a  late-stage  isotopic  exchange  with  complete  and  selective  isotopic  labelling.
■590    ▼aSchool  code:  0054.
■650  4▼aOrganic  chemistry
■650  4▼aChemistry
■653    ▼aDeaminative  alkylation
■653    ▼aAlkyl  amines
■653    ▼aPhotoredox  catalysis
■690    ▼a0490
■690    ▼a0485
■71020▼aColumbia  University▼bChemistry.
■7730  ▼tDissertations  Abstracts  International▼g85-12B.
■790    ▼a0054
■791    ▼aPh.D.
■792    ▼a2024
■793    ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17162523▼nKERIS▼z이  자료의  원문은  한국교육학술정보원에서  제공합니다.

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