Abstract:

My thesis research developed fluorescence microscopy as a tool to overcome prior analytical limitations that created difficulties studying the reaction of organohalides with zinc metal to form organozinc complexes. Fluorescence microscopy methods for the observation of organozinc intermediates under reaction conditions have now been expanded, harnessed, and further developed to provide insight into four systems: 1) An origin of batch-to-batch variation in organoindium synthesis, 2) Solvent effects in organozinc synthesis, 3) Salt effects in Rieke zinc systems, 4) Effect of TMSCl pretreatment on commercial zinc powder, and 5) Environment heterogeneity of commercial zinc powder during oxidative addition. To enable insight into the mechanisms of activators with zinc metal, imaging experiments were taken into a new direction—fluorescence lifetime imaging microscopy (FLIM)—which had not previously been used to study oxidative addition of organohalides to metal surfaces. Together, the findings in this dissertation could lead to targeted improvement of the synthesis of organozinc reagents and to the activation of currently unreactive metals beyond zinc.