Date of Award

12-14-2017

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

Hao Xu

Abstract

This dissertation is concerned about four types of iron-catalyzed selective nitrogen atom transfer reactions developed in Xu group during 2012 and 2017, which can facilitate efficient access to valuable functional molecules from readily available petro-chemicals and other abundant starting olefinic materials. These iron-catalyzed stereoselective olefin difunctionalization processes include intermolecular olefin amino-oxygenation, amino-fluorination and trifluoromethyl azidation.

Compared to all other existing methods, our strategies have a broader substrate scope as well as improved or complementary selectivity in terms of regioslectivity, diastereoselectivity and enantioselectivity. To achieve a fine balance between catalyst reactivity, stability, and reaction selectivity, we explored a variety of iron catalysts, ligands and new amination reagents. Our methods allow chemists to conveniently transform a broad range of simple, abundant olefin precursors to a variety of functionalized vicinal amino alcohols and vicinal fluoro primary amines that are valuable in both organic synthesis and biomedical sciences.

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