Date of Award

5-9-2016

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

Dr. Hao Xu

Second Advisor

Dr. Alfons Baumstark

Third Advisor

Dr. Jun Yin

Fourth Advisor

Dr. Ivaylo Ivanov

Abstract

Numerous biologically active alkaloids and pharmaceuticals contain nitrogen atoms that are directly attached to stereogenic centers. Therefore, selective nitrogen atom transfer to readily available hydrocarbons through novel mechanistic pathways is an important tool for the synthesis of high-value functional molecules. We are interested in direct difunctionalization of alkenes with non-precious iron catalyst due to its advantages over well-established olefin aziridination and direct C-H amination methods in organic synthesis. Herein, we describe iron-catalyzed nitrogen atom transfer methods for stereoselective olefin difunctionalization, including olefin aminohydroxylation and diamination reactions. These transformations capitalize on the novel reactivity of iron catalysts by conveniently converting petrochemicals to highly functionalized building blocks that are valuable to organic synthesis, material and biomedical sciences.

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