A new method utilizing a Ru-catalyzed pyridine-promoted CCl<sub>4</sub>-based system was developed to synthesize protected carboxylic acids through the oxidation of silyl ethers to silyl esters. Conventional heating methods were previously optimized to favor the target silyl ester over the carboxylic acid side product, and temperature, solvent ratio, and catalyst loading were also optimized for microwave heating. A solvent screening indicated EtOAc as a less toxic alternative to CCl<sub>4</sub>; the variation in the reactivity observed within each solvent system provided mechanistic insights regarding the formation of carboxylic acid. The mechanistic role of the promoter was also explored to determine if pyridine acted as a ligand or a base. Scope studies were performed testing various functional groups and silyl groups ranging in size and stability. The functional groups tested were esters, ketones, epoxides, tertiary alcohols, nitro groups, nitriles, halides, alkenes, alkynes, and aryl groups.

Ru-catalyzed pyridine-promoted oxidation of silyl ethers to silyl esters

2019 Spring National Meeting

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