Copper-Catalyzed 1,2-Aminocarbonation of Unactivated Alkenes Utilizing O-Benzoylhydroxylamines

Ph.D. Defense Qiu Wang, Ph.D, Advisor Abstract: My doctoral work has focused on alkene difunctionalization, a powerful synthetic method that can transform simple alkene feedstocks into richly functionalized valuable skeletons. With the ubiquitous nature of nitrogen-containing molecules in organic synthesis, pharmaceuticals, and materials, the development of robust alkene amination functionalization strategies has been of utmost interest. Despite extensive progress in this area, the general approach for aminocarbonation of alkenes remains underdeveloped. To fill this gap, I have devoted my effort to developing copper-catalyzed 1,2-aminocarbonation strategies using O-benzoylhydroxylamines as electron-rich amine radical precursors, which would initiate the amination of unactivated alkenes followed by installation of various carbon functional groups via distal migration. Through these efforts, I have established synthetic methods that allow access to a broader range of structurally complex skeletons possessing electron-rich secondary or tertiary amines as well as valuable carbon functional groups.