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Alcohol Deoxygenation for the Synthesis of C(sp3) Rich Organic Molecules
Alcohol Deoxygenation for the Synthesis of C(sp3) Rich Organic Molecules
Alcohol Deoxygenation for the Synthesis of C(sp3) Rich Organic Molecules

상세정보

자료유형  
 학위논문 서양
최종처리일시  
20250211151442
ISBN  
9798382807638
DDC  
547
저자명  
Intermaggio, Nicholas Edward.
서명/저자  
Alcohol Deoxygenation for the Synthesis of C(sp3) Rich Organic Molecules
발행사항  
[Sl] : Princeton University, 2024
발행사항  
Ann Arbor : ProQuest Dissertations & Theses, 2024
형태사항  
373 p
주기사항  
Source: Dissertations Abstracts International, Volume: 85-12, Section: B.
주기사항  
Advisor: MacMillan, David W. C.
학위논문주기  
Thesis (Ph.D.)--Princeton University, 2024.
초록/해제  
요약Synthetic methods that enable rapid construction of complex organic molecules from simple precursors are of paramount importance to human health. Given their structural diversity and ubiquity amongst a variety of natural sources, harnessing alcohols as starting materials in chemical synthesis would provide access to underexplored chemical space. In particular, cleavage of an alcohol C-O bond and subsequent formation of new C-C bonds represents a powerful strategy for complex molecule synthesis. Traditional deoxygenation protocols require harsh reaction conditions or laborious prefunctionalization that limits their utility. Photoredox catalysis has provided of a suite of methods for the cleavage of alcohol C-O bonds, including the discovery of benzoxazolium salts (termed NHCs) as in situ activating reagents.This thesis describes the utilization of these benzoxazolium salts to convert alcohols to C(sp3 )-CF3 and C(sp3 )-C(sp3 ) bonds. Chapter 2 discusses the conversion of alcohols to aliphatic trifluoromethyl groups by merging NHC deoxygenation with copper metallaphotoredox catalysis. Chapter 3 details a first of its kind cross alcohol coupling reaction that is enabled by combining NHC alcohol activation with the principles of SH2 radical sorting.
일반주제명  
Organic chemistry
일반주제명  
Chemistry
일반주제명  
Biochemistry
키워드  
Human health
키워드  
Benzoxazolium salts
키워드  
Alcohol
키워드  
Natural sources
키워드  
Deoxygenation protocols
기타저자  
Princeton University Chemistry
기본자료저록  
Dissertations Abstracts International. 85-12B.
전자적 위치 및 접속  
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■040    ▼aMiAaPQ▼cMiAaPQ
■0820  ▼a547
■1001  ▼aIntermaggio,  Nicholas  Edward.▼0(orcid)0009-0006-6193-6891
■24510▼aAlcohol  Deoxygenation  for  the  Synthesis  of  C(sp3)  Rich  Organic  Molecules
■260    ▼a[Sl]▼bPrinceton  University▼c2024
■260  1▼aAnn  Arbor▼bProQuest  Dissertations  &  Theses▼c2024
■300    ▼a373  p
■500    ▼aSource:  Dissertations  Abstracts  International,  Volume:  85-12,  Section:  B.
■500    ▼aAdvisor:  MacMillan,  David  W.  C.
■5021  ▼aThesis  (Ph.D.)--Princeton  University,  2024.
■520    ▼aSynthetic  methods  that  enable  rapid  construction  of  complex  organic  molecules  from  simple  precursors  are  of  paramount  importance  to  human  health.  Given  their  structural  diversity  and  ubiquity  amongst  a  variety  of  natural  sources,  harnessing  alcohols  as  starting  materials  in  chemical  synthesis  would  provide  access  to  underexplored  chemical  space.  In  particular,  cleavage  of  an  alcohol  C-O  bond  and  subsequent  formation  of  new  C-C  bonds  represents  a  powerful  strategy  for  complex  molecule  synthesis.  Traditional  deoxygenation  protocols  require  harsh  reaction  conditions  or  laborious  prefunctionalization  that  limits  their  utility.  Photoredox  catalysis  has  provided  of  a  suite  of  methods  for  the  cleavage  of  alcohol  C-O  bonds,  including  the  discovery  of  benzoxazolium  salts  (termed  NHCs)  as  in  situ  activating  reagents.This  thesis  describes  the  utilization  of  these  benzoxazolium  salts  to  convert  alcohols  to  C(sp3  )-CF3  and  C(sp3  )-C(sp3  )  bonds.  Chapter  2  discusses  the  conversion  of  alcohols  to  aliphatic  trifluoromethyl  groups  by  merging  NHC  deoxygenation  with  copper  metallaphotoredox  catalysis.  Chapter  3  details  a  first  of  its  kind  cross  alcohol  coupling  reaction  that  is  enabled  by  combining  NHC  alcohol  activation  with  the  principles  of  SH2  radical  sorting.
■590    ▼aSchool  code:  0181.
■650  4▼aOrganic  chemistry
■650  4▼aChemistry
■650  4▼aBiochemistry
■653    ▼aHuman  health
■653    ▼aBenzoxazolium  salts
■653    ▼aAlcohol
■653    ▼aNatural  sources
■653    ▼aDeoxygenation  protocols
■690    ▼a0490
■690    ▼a0487
■690    ▼a0485
■71020▼aPrinceton  University▼bChemistry.
■7730  ▼tDissertations  Abstracts  International▼g85-12B.
■790    ▼a0181
■791    ▼aPh.D.
■792    ▼a2024
■793    ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17161765▼nKERIS▼z이  자료의  원문은  한국교육학술정보원에서  제공합니다.

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