8th Annual WML Academic Symposium

Presenter(s): Houston Cole and Alisha Weinhofe
Title: Pyridine-Promoted Ruthenium-Catalyzed Oxidation of Silyl Ethers to Silyl Esters
Developed under the guidance of Dr. Sarah Goforth , Chemistry

A biphasic ruthenium-catalyzed oxidation system was utilized for the transformation of silyl ethers to silyl esters. The reaction was optimized for conversion and for selectivity of the silyl ester over a carboxylic acid side product. The mechanism for the formation of the carboxylic acid, previously hypothesized to occur through simple hydrolysis of the silyl ester product, was discovered to have an additional solvent-dependent pathway resulting in stable equilibrium amounts of the two products. The mechanistic role of pyridine is also being explored, and substrates with a variety of common functional groups and silyl groups are being tested.