Oxidative Palladium(II)-catalyzed Arene C-H Bond Functionalization and Progress towards the Total Synthesis of 6-Deoxyerythronolide B
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Chemistry dissertation on palladium-catalyzed C-H functionalization and a total synthesis; synthetic methodology in the bench sense, not research practice.
The dissertation studies chemical synthesis and catalytic reactions rather than research methods as an object.
Chemistry dissertation on palladium-catalyzed arene C–H functionalization and natural-product synthesis.
Résumé
To address the issue of unnecessary functional group transformations in synthesis, the direct functionalization of carbon-hydrogen (CâH) bonds presents itself as an efficient and atom economical process. In particular, palladium(II)-catalyzed oxidative functionalization of arene CâH bonds were investigated to yield intermolecular and intramolecular arylations. Kinetic studies and characterization of bimetallic palladium(II) complexes led to the discovery of two other palladium(II)-catalyzed processes: arene hydroxylation and selective chlorination of anilides.\nRealizing the potential of biocatalysis and of transition-metal catalysis, we marriaged these two fundamentally different methods to access complex molecules in rapid and step economical ways and chose popular synthetic target, 6-deoxyerythronolide B to showcase the efficiency of these stereoselective reactions. To form the 14-membered lactone, we employed a transition-metal catalyzed ring-closing metathesis. Two different fragments were assembled via traditional and reliable aldols, oxidations and reductions, crotylations and protective group chemistry.
Conservé avec la notice de tri, où il sert de preuve aux étiquettes ci-dessus.
La notice
- Revue
- Library and Archives Canada (Government of Canada)
- Thématique
- Catalytic C–H Functionalization Methods
- Domaine
- Chemistry
- Établissements canadiens
- —
- Organismes subventionnaires
- Natural Sciences and Engineering Research Council of Canada
- Mots-clés
- ChemistryPalladiumCatalysisIntramolecular forceMetathesisSurface modificationBimetallic stripCombinatorial chemistryAlkeneReductive eliminationOxidative additionHydroxylationTotal synthesisOrganic chemistryPolymerization
- Résumé présent dans OpenAlex
- oui