UBC Theses and Dissertations
Nickel-catalyzed decarbonylative coupling for access to biaryl motifs LaBerge, Nicole
The goal of this research project was to design a sustainable catalytic cross-coupling reaction using nickel and carboxylic acid derivatives and apply it to the synthesis biaryls. A low-cost route to a variety of functionalized bis(hetero)aryl and biaryl motifs has been developed using aryl esters and boronic acids. This Suzuki-Miyaura-type decarbonylative cross- coupling is catalyzed by an affordable low-toxic catalyst system composed of Ni(cod)2 and PCy3. Electron-rich arylboronic acids gave the highest yields. A variety of functional groups including methyl ethers, esters, fluorine substituents and acetals are compatible with the reaction conditions. The reaction did not tolerate boronic acids possessing halogen or cyano functionalities. Aryl esters with and without nitrogen atoms were also accommodated in the reaction. The methodology reveals challenges associated with nickel and esters in cross- coupling chemistry. Additionally, it presents an attractive alternative to the use of palladium catalysis currently used in industry to acquire such biaryls.
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Attribution-NonCommercial-NoDerivs 2.5 Canada