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Nickel-Catalyzed Site- and Stereoselective Syntheses of Complex Molecular Fragments From 1,3-Dienes Through Use of Novel P,N Ligands
Nickel-Catalyzed Site- and Stereoselective Syntheses of Complex Molecular Fragments From 1...
Nickel-Catalyzed Site- and Stereoselective Syntheses of Complex Molecular Fragments From 1,3-Dienes Through Use of Novel P,N Ligands

Detailed Information

자료유형  
 학위논문 서양
최종처리일시  
20260202104803
ISBN  
9798291554319
DDC  
547
저자명  
Mickles, Devin T.
서명/저자  
Nickel-Catalyzed Site- and Stereoselective Syntheses of Complex Molecular Fragments From 1,3-Dienes Through Use of Novel P,N Ligands
발행사항  
[Sl] : The University of North Carolina at Chapel Hill, 2025
발행사항  
Ann Arbor : ProQuest Dissertations & Theses, 2025
형태사항  
123 p
주기사항  
Source: Dissertations Abstracts International, Volume: 87-02, Section: B.
주기사항  
Advisor: Johnson, Jeffrey S.
학위논문주기  
Thesis (Ph.D.)--The University of North Carolina at Chapel Hill, 2025.
초록/해제  
요약Alkenes are abundant feedstock chemicals which can be utilized as platforms for the construction of complex molecules bearing a variety of functional groups and stereogenic centers. Methods which focus on facilitating this rapid development of complexity while exerting site- and stereocontrol are of great importance. Olefin dicarbofunctionalization is a general reaction class which allows for the formation of two new C-C σ-bonds from an olefin π-bond allowing for a step and atom economical means of accessing functionalized molecules. Homoallylation reactions have also received attention as a means of synthesizing understudied bishomoallyl alcohols and amines from simple dienes and either aldehydes or imine substrates.Chapter 1 describes early work conducted on the dicarbofunctionalization of 1,3-alkyl dienes with aldehydes. While 1,3-alkyl dienes pose numerous challenges for selective couplings due to their smaller size, we were able to observe an improvement in site-selectivity when employing a novel pyridylphosphine ligand.Chapter 2 demonstrates the effective use of pyridylphosphine ligands in the site- and stereoselective dicarbofunctionalization of 1,3-dienes with imines and boronic ester coupling partners. We also determined that the site-selectivity of the reaction can be guided by additional substitution of the diene to form all-carbon quaternary centers selectively.Chapter 3 covers our current progress on the homoallylation of aldehydes with 1,3-dienes to form bishomoallylic alcohols. Use of our P,N ligand system allows for use non-polarized dienes for the selective synthesis of all-carbon quaternary center containing alcohol products.
일반주제명  
Organic chemistry
일반주제명  
Chemistry
일반주제명  
Analytical chemistry
키워드  
Dicarbofunctionalization
키워드  
Alkenes
키워드  
Pyridylphosphine ligands
키워드  
Homoallylation
키워드  
Molecular fragments
기타저자  
The University of North Carolina at Chapel Hill Chemistry
기본자료저록  
Dissertations Abstracts International. 87-02B.
전자적 위치 및 접속  
로그인 후 원문을 볼 수 있습니다.

MARC

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■020    ▼a9798291554319
■035    ▼a(MiAaPQ)AAI32164880
■040    ▼aMiAaPQ▼cMiAaPQ
■0820  ▼a547
■1001  ▼aMickles,  Devin  T.
■24510▼aNickel-Catalyzed  Site-  and  Stereoselective  Syntheses  of  Complex  Molecular  Fragments  From  1,3-Dienes  Through  Use  of  Novel  P,N  Ligands
■260    ▼a[Sl]▼bThe  University  of  North  Carolina  at  Chapel  Hill▼c2025
■260  1▼aAnn  Arbor▼bProQuest  Dissertations  &  Theses▼c2025
■300    ▼a123  p
■500    ▼aSource:  Dissertations  Abstracts  International,  Volume:  87-02,  Section:  B.
■500    ▼aAdvisor:  Johnson,  Jeffrey  S.
■5021  ▼aThesis  (Ph.D.)--The  University  of  North  Carolina  at  Chapel  Hill,  2025.
■520    ▼aAlkenes  are  abundant  feedstock  chemicals  which  can  be  utilized  as  platforms  for  the  construction  of  complex  molecules  bearing  a  variety  of  functional  groups  and  stereogenic  centers.  Methods  which  focus  on  facilitating  this  rapid  development  of  complexity  while  exerting  site-  and  stereocontrol  are  of  great  importance.  Olefin  dicarbofunctionalization  is  a  general  reaction  class  which  allows  for  the  formation  of  two  new  C-C  σ-bonds  from  an  olefin  π-bond  allowing  for  a  step  and  atom  economical  means  of  accessing  functionalized  molecules.  Homoallylation  reactions  have  also  received  attention  as  a  means  of  synthesizing  understudied  bishomoallyl  alcohols  and  amines  from  simple  dienes  and  either  aldehydes  or  imine  substrates.Chapter  1  describes  early  work  conducted  on  the  dicarbofunctionalization  of  1,3-alkyl  dienes  with  aldehydes.  While  1,3-alkyl  dienes  pose  numerous  challenges  for  selective  couplings  due  to  their  smaller  size,  we  were  able  to  observe  an  improvement  in  site-selectivity  when  employing  a  novel  pyridylphosphine  ligand.Chapter  2  demonstrates  the  effective  use  of  pyridylphosphine  ligands  in  the  site-  and  stereoselective  dicarbofunctionalization  of  1,3-dienes  with  imines  and  boronic  ester  coupling  partners.  We  also  determined  that  the  site-selectivity  of  the  reaction  can  be  guided  by  additional  substitution  of  the  diene  to  form  all-carbon  quaternary  centers  selectively.Chapter  3  covers  our  current  progress  on  the  homoallylation  of  aldehydes  with  1,3-dienes  to  form  bishomoallylic  alcohols.  Use  of  our  P,N  ligand  system  allows  for  use  non-polarized  dienes  for  the  selective  synthesis  of  all-carbon  quaternary  center  containing  alcohol  products.
■590    ▼aSchool  code:  0153.
■650  4▼aOrganic  chemistry
■650  4▼aChemistry
■650  4▼aAnalytical  chemistry
■653    ▼aDicarbofunctionalization
■653    ▼aAlkenes
■653    ▼aPyridylphosphine  ligands
■653    ▼aHomoallylation
■653    ▼aMolecular  fragments
■690    ▼a0490
■690    ▼a0486
■690    ▼a0485
■71020▼aThe  University  of  North  Carolina  at  Chapel  Hill▼bChemistry.
■7730  ▼tDissertations  Abstracts  International▼g87-02B.
■790    ▼a0153
■791    ▼aPh.D.
■792    ▼a2025
■793    ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17358867▼nKERIS▼z이  자료의  원문은  한국교육학술정보원에서  제공합니다.

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