Abstract: Traditional methods to perform cyclopropane synthesis typically utilize carbenoid intermediates or other nucleophiles reacting with olefins to form two C–C bonds in a single reaction. In order to expand the chemical space of these syntheses, it is necessary to find orthogonal techniques that offer new ways to access similar products and stereochemical outcomes as these methods. One way to accomplish this is by using alcohols, one of the most prevalent functional groups in chemistry, as a starting material. Alcohols will readily generate electrophiles, such as sulfonates and halides, that can be activated by transition metals. Methods utilizing this reactivity will be reported to perform cross-electrophile coupling reactions that generate cyclopropanes.