Date of Award

8-11-2015

Degree Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Hao Xu

Second Advisor

Alfons Baumstark

Third Advisor

Ivaylo Ivanov

Abstract

The first chapter of the thesis describes an iron(II)-catalyzed intermolecular amino-oxygenation of alkenes. This amino-oxygenation method is found to be compatible with a broad range of synthetically valuable alkenes and affords the corresponding 1,2-amino alcohols with excellent regio- and diastereoselectivity. Additionally, practical synthetic procedures for the amino-oxygenation of styrene, a fully functionalized glycal, and indene are described. The second chapter of the thesis describes a regioselective and diastereoselective iron(II)-catalyzed intermolecular aminofluorination of alkenes using nucleophilic fluorinating reagents. This method affords new vicinal amino fluorides that were previously difficult to prepare. In both the amino-oxygenation and aminofluorination reactions, bench-stable hydroxylamine derivatives functioned as both the oxidant and amination reagents. Preliminary mechanistic studies suggested that an iron-nitrenoid is a possible reactive intermediate on both reaction pathways. These new difunctionalization strategies represent efficient alternatives to current amino-oxygenation and aminofluorination methods.

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