The goal of our research was to synthesize a series of carbohydrate porphyrin conjugates using alkyl linkers of varying length. These alkyl linkers were coupled to a halogenated porphyrin using a palladium-catalyzed C-O cross-coupling reaction. This cross-coupling reaction was conducted on a brominated-metalloporphyrin and an alkynylated alcohol in the presence of a palladium catalyst, phosphine ligand, and a base at an elevated temperature to ensure its conversion into an alkoxy-substituted zinc diphenyl-porphyrin (ZnDPP). Optimization of reaction conditions were required to establish a method that produced the highest overall product formation. Each alkynylated alcohol employed contained a linkage of 2-6 carbons between the oxygen and the alkyne group which was protected with a trimethylsilyl (TMS) group.<sup> </sup>The resulting protected alkynylated diphenyl-porphyrin is then deprotected using standard procedures found in literature. The deprotected alkynylated DPP can be then used to undergo a variety of transformations to create an assortment of derivatized porphyrins.

Alkoxy-substituted diphenyl-porphyrin synthesis utilizing palladium-catalyzed C-O cross coupling

2019 Spring National Meeting

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