Development of neutral redox carbon-carbon bond forming reactions via transition metal-catalyzed transfer hydrogenation

Since C–C bonds form the backbone of every organic molecule and reside at the heart of chemical science, the development of new efficient methods for promoting C–C bond formation is of great significance. Inspired and expanded from traditional Grignard reactions, the work presented in this dissertation focuses on metal catalyzed neutral redox-triggered carbonyl addition via transfer hydrogenation. Advancing the native reducing capability of alcohols, employment of catalytic transition metals enables the formation of nucleophile-electrophile pairs in situ, en route to the products of formal alcohol C–H functionalization. These redox-triggered reactions circumvent the stoichiometric metallated byproduct waste and streamline the construction of complex molecules from simple and/or readily available feedstocks. The research reported herein discloses new developed methodologies of ruthenium and iridium catalyzed coupling reactions of primary and secondary alcohols with various pi-unsaturates. These studies contribute to the growing body of redox-triggered alcohol C–C couplings – new carbonyl addition chemistry that extends beyond the use of premetalated reagents.