The Discovery, Development, and Mechanistic Investigations of Transition Metal-Catalyzed Organic Reactions

Thesis (Ph.D.)--University of Washington, 2016-06

Organic reactions have wide spread applications in drug development, chemical biology, and materials science. However, traditional chemical techniques can be inefficient i.e., low yields and/or poor selectivity, for constructing structurally complex motifs and for selectively activating strong bonds. To address these problems, there has been an increasing focus on developing new organic reactions catalyzed by transition metals. This document describes my contributions to transition metal catalysis and includes the following works: 1) Catalytic activation of a single C-F bond in trifluoromethyl arenes for the synthesis of difluoromethyl arenes, 2) Mild copper-catalyzed fluorination of alkyl triflates using potassium fluoride, 3) Copper-catalyzed reduction of alkyl triflates and iodides: an efficient method for the deoxygenation of primary and secondary alcohols, 4) Synthesis of hindered anilines, and 5) Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes. For each work, I will describe its significance to organic synthesis, its discovery and development, and the investigation of its mechanism.