Pan, Zhongda2017-03-142017-03-142016-11https://hdl.handle.net/11299/185147University of Minnesota Ph.D. dissertation. November 2016. Major: Chemistry. Advisor: Christopher Douglas. 1 computer file (PDF); xiii, 284 pages.This Thesis describes the development of transition-metal-catalyzed alkene additions reactions through the activation of C–C and C–heteroatom σ-bonds. In these transformations, a C–C or C–heteroatom σ-bond is activated, cleaved, and added across an alkene double bond without inducing fragmentation, allowing addition of an alkene with vicinal functional groups and rapid construction of carbo- and heterocycles in an atom-economical manner. Chapter 1 provides an overview of catalytic alkene addition reactions and C–C σ-bond activation reactions. Chapters 2, 3, and 5 describe alkene addition reactions by catalytic activation of C–CN, C–O, and N–CN σ-bonds, respectively. An unprecedented metal-free N–CN bond cleavage process is discussed in Chapter 4.enDevelopment of Catalytic C–CN, C–O, and N–CN Sigma-Bonds Activation and Alkene Addition ReactionsThesis or Dissertation