Transition metal catalysed C-C bond formation via C-H functionalisation

Thesis

The functionalisation of C-H bonds has been widely studied in organic synthesis. This work presents the results of investigation into two areas of current research, copper-catalysed aromatic C-H functionalisation and rhodium-catalysed hydroacylation. Chapter 1 presents the development of palladium- and copper-catalysed aromatic C-H functionalisation with particular attention paid to regiocontrol. Chapter 2 describes the development of copper-catalysed cross-coupling of perfluorinated arenes and alkenyl halides along with efforts to expand this methodology to a more general reaction. In Chapter 3 the development of chelation-controlled rhodium-catalysed hydroacylation is discussed. Chapter 4 outlines the utilisation of amino acid derived N-methylthiomethyl aldehydes in rhodium-catalysed hydroacylation methodology.

Authors: Truscott, FR

• Publication date: 2012
• DOI: 10.5287/ora-aegrpwk64
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: University of Oxford
• Language: English
• Keywords: rhodium; C-C bond formation; copper; C-H functionalisation; hydroacylation; cross coupling
• Subjects: Synthetic organic chemistry; Catalysis; Organometallic Chemistry; Organic synthesis; Chemistry & allied sciences; Organic chemistry