The Direct Pd-Catalyzed C(sp3)–H Functionalization of Aliphatic Carboxylic Acids
The functionalization of C(sp³)–H bonds has become a key strategy in modern organic synthesis, enabling the efficient construction of complex molecules from simple precursors. In this thesis, I introduced the fundamental principles of C(sp³)–H activation, summarizing prior advancements, limitations, and ongoing efforts in the field. Chapter 2 explores β-C(sp³)–H amination of free carboxylic acids. Despite extensive optimization, the desired β-amino acid products were not obtained, but the findings provide insights for future research. Chapter 3 presents a palladium-catalyzed β-C(sp³)–H hydroxylation, enabled by pyridone-based ligands. This method shows broad functional group tolerance and works well with α-non-quaternary carboxylic acids. Chapter 4 describes γ-C(sp³)–H lactonization using sodium percarbonate and a β-alanine-derived ligand. This one-step reaction efficiently converts various carboxylic acids, including β-non-quaternary substrates, into γ-lactones, offering a valuable tool for synthesis.
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