Formation of carbon-heteroatom bonds remains a significant challenge in modern organic chemistry. One strategy is to oxidize nucleophiles such as boronic acids and esters or silicates in transformations such as the Chan-Lam Coupling or the Fleming-Tamao Oxidation. We have optimized the synthesis of bis(ethyleneglycol)silicates, which have only been proposed as an intermediate in a modified Hiyama Coupling. We have also shown that these silicates can be oxidized to form several different types of carbon-heteroatom bonds. Notably, we can oxidize aryl silanes under fluoride-free conditions; there are few reports of this particular transformation. Herein, we report the fluoride-free oxidation aryl-Si bonds to make aryl-O bonds, including phenols and esters. We are also working towards creating aryl-N bonds through a silicate oxidation. Optimization and substrate scope will be discussed.

Synthesis and oxidation of potassium bis(ethyleneglycol)organosilicates

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