The project aims to streamline the synthesis of 2,2’-bipyridine adducts, so they can be efficiently synthesized as precursors for ligands in novel organometallic ruthenium complexes. Specifically, the compounds being synthesized are 4-methylated and 4,4’-dimethylated 2,2’-bipyridines. Three different synthetic methods are explored, including homo-coupling and cross-coupling reactions, as well as the use of a turbo-Grignard reagent. The homo-coupling reaction with or without the turbo-Grignard reagent uses only the 2-bromo-4-methyl pyridine as the starting material to produce the 4,4’-dimethylated adduct, versus the cross-coupling reaction which utilizes a combination of the 2-bromo-4-methyl pyridine and the trimethylstannyl pyridine substrates to produce the 4-methylated adduct. The methodology has been developed to ensure an air-free environment by assembling the closed reaction chamber in a nitrogen glovebox. All reactions are completed on a Schlenk-line assembly under inert argon atmosphere and are monitored by TLC. The products are isolated and purified via extraction and sublimation. Compound characterization is carried out by utilizing NMR and FT-IR spectroscopy. The bipyridine building blocks, based on their excellent complexing abilities as bidentate ligands, will be incorporated into ruthenium complexes in a collaborative project. The increased photosensitivity of these complexes could lead to many practical applications, ranging from synthetic photovoltaics to anti-cancer activity.

Comparing efficiencies of organometallic coupling reactions to create 2,2’-bipyridine adducts

2019 Spring National Meeting

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