Repository logo

Infoscience

  • English
  • French
Log In
Logo EPFL, École polytechnique fédérale de Lausanne

Infoscience

  • English
  • French
Log In
  1. Home
  2. Academic and Research Output
  3. EPFL thesis
  4. Investigation of palladium(IV) species in organic synthesis and synthetic studies towards meloyunnanine A
 
doctoral thesis

Investigation of palladium(IV) species in organic synthesis and synthetic studies towards meloyunnanine A

Fujii, Takuji  
2024

This dissertation addresses two research themes in modern organic synthesis. The first topic explores the development of new reactions enabled by Pd(IV)-involved catalytic cycles. The second theme investigates the synthetic studies towards total synthesis of meloyunnanine A. Our group recently disclosed a first example of a catalytic dyotropic rearrangement of Pd(IV) species, representing a novel approach to activating Câ C bonds. In chapter 1, we describe the general background of Pd(IV) chemistry and our efforts to identify other examples involving the novel migration of Câ Pd(IV) bonds in domino reactions. (1) Firstly, a dyotropic rearrangement in a domino process initiated by β-C(sp3)â H bond activation of amides bearing a quaternary carbon was investigated. A broad range of saturated morpholine amides was converted to α,β-unsaturated amides as an outcome of editing their quarternary carbons. Mechanistically, it is noteworthly that the domino process contained an unprecedented 1,3-Pd(IV) shift. (2)

  • Files
  • Details
  • Metrics
Type
doctoral thesis
DOI
10.5075/epfl-thesis-11007
Author(s)
Fujii, Takuji  

EPFL

Advisors
Zhu, Jieping  
Jury

Prof. Jérôme Waser (président) ; Prof. Jieping Zhu (directeur de thèse) ; Prof. Nicolai Cramer, Prof. Tim Donohoe, Prof. Johannes Wahl (rapporteurs)

Date Issued

2024

Publisher

EPFL

Publisher place

Lausanne

Public defense year

2024-10-28

Thesis number

11007

Total of pages

327

Subjects

Rearrangement

•

Oxidation

•

Reductive elimination

•

Palladium

•

Amide

•

Norbornene

•

Dihydrofuran

•

Benzocyclobutene

•

Iminium

•

Meloyunnanine A

EPFL units
LSPN  
Faculty
SB  
School
ISIC  
Doctoral School
EDCH  
Available on Infoscience
October 21, 2024
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/241663
Logo EPFL, École polytechnique fédérale de Lausanne
  • Contact
  • infoscience@epfl.ch

  • Follow us on Facebook
  • Follow us on Instagram
  • Follow us on LinkedIn
  • Follow us on X
  • Follow us on Youtube
AccessibilityLegal noticePrivacy policyCookie settingsEnd User AgreementGet helpFeedback

Infoscience is a service managed and provided by the Library and IT Services of EPFL. © EPFL, tous droits réservés