Palladium-catalysed heterocycle synthesis

Thesis

Chapter 1 is a literature review of selected palladium-catalysed aryl C-N and C-S bond forming reactions. The application of these reactions to the synthesis of heterocycles is also discussed.

Chapter 2 highlights the importance of the benzimidazole motif and gives a brief discussion of the existing routes to this scaffold. The utility of N-(o-halophenyl)imidoyl chlorides and imidates as precursors to heterocycles is demonstrated in a palladium-catalysed reaction with N-nucleophiles to afford benzimidazole products.

Chapter 3 provides a brief introduction to the synthesis of benzothiazoles and describes efforts towards the use of our established substrates for the preparation of these heterocycles. This is achieved via reaction of N-(o-chlorophenyl)imidoyl chlorides with a sulfur nucleophile in a metal-free process.

Chapter 4 is a literature review of palladium-catalysed carbonylation chemistry with specific focus on aminocarbonylation and thiocarbonylation reactions of aryl halides. Heterocycle syntheses which employ such carbonylative methods are also discussed.

Chapter 5 describes existing protocols for the synthesis of quinazolinones. A novel palladium-catalysed synthesis of these heterocycles from the reaction of our imidate substrates with an amine and carbon monoxide is described. This further demonstrates their utility as general heterocycle precursors

Authors: Sadig, JER

• Publication date: 2012
• DOI: 10.5287/ora-aqqm25yab
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: University of Oxford
• Language: English
• Keywords: palladium; heterocycles; catalysis
• Subjects: Organometallic Chemistry; Catalysis; Organic chemistry