Novel decarboxylative methods for carbon bond formation

Abstract

Carboxylic acids are naturally and commercially abundant materials. In fact, compared to other commonly used organic starting materials (organoborons, organoiodides, organobromides and organochlorides) used for synthesis, carboxylic acids are over four times more abundant, with nearly 1.6 million commercially available derivatives. Therefore, there has been a large pursuit of methods to efficiently form new bonds through decarboxylative functionalization in modern literature. This thesis will contain three main areas of research involving the decarboxylation of carboxylic acids to perform 1) C(sp3)-C(sp3) bond formation, 2) trifluoromethylation, and 3) aryne formation. The first two chapters will revolve around the use of redox-active esters to synthesize alkyl-alkyl bonds that are relevant to pharmaceuticals. The remaining chapters will look into the design and synthesis of a novel aryne precursor that is conveniently activated and diversified under mild conditions.