Remote Activation Strategies for O-Glycosylation and C-H Functionalization
Justin R. Ragains, Associate Professor of Chemistry, Dept. of Chemistry, Louisiana State University
Abstract: For the past few years, two major areas of interest in our group have been O-glycosylation and C-H functionalization. While these represent fairly disparate areas of study in organic synthesis, we have demonstrated that remote activation can be an effective strategy for accomplishing both classes of transformation. In particular, we have demonstrated two approaches to thioglycoside activation involving either visible-light irradiation or protonation of a pendant styrene. Further, the protonation strategy may provide a robust alternative to glycosyl trichloroacetimidates, a workhorse in the area of O-glycosylation. In the area of C-H functionalization, we have shown that intramolecular hydrogen atom transfer from an sp3-hybridized carbon to an aryl radical can precede oxidation of the resulting alkyl radical to carbocation and nucleophilic attack. We have demonstrated C-H hydroxylation, etherification, amidation, and a novel synthesis of the antidepressant fluoxetine using this strategy.
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