Investigation of silicon Lewis acidity and design of a novel silicon Lewis acid catalyst scaffold
Zielinski, Matthew Edward
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Lewis acids have been a cornerstone in modern organic synthesis, but the use of silicon Lewis acids has not received as much attention. Silicon Lewis acids have unique features that differ from some typical metal catalysts. Some of these properties include good solubility in organic solvents, decreased likelihood for ligand exchange, and decreased toxicity. These differences make the use of silicon Lewis acids a versatile tool for organic synthesis. There is a great deal yet to explore about silicon Lewis acidity and silicon Lewis acids and from that two main projects arose in order to further study these concepts.Preparation of a small library of silyloxybenzaldehydes allowed for the design of a chemical probe to investigate if the groups have any influence on the neighboring carbonyl group. The most common use for silicon in organic chemistry is where some trialkyl silicon moiety serves as a protecting group. This probe looks to rethink the current silicon protecting group archetype. Taking concepts learned from this chemical probe and from literature it is proposed that a novel silicon Lewis acid scaffold can be constructed. This silicon Lewis acid scaffold would be easily modifiable and tunable and have great potential on future catalyst design.