Abstract:

Cross-coupling and cross-electrophile coupling reactions are versatile and powerful ways to form carbon-carbon bonds. Identifying novel pathways, technologies, and reagents that can be used in these critical reactions allows the expansion of accessible chemical space. First, a mechanistic investigation of a cross-electrophile coupling will be presented. The reaction was identified to proceed through two diverging mechanisms, with each mechanism leading to a different stereochemical outcome. Then, an electrochemical cross-electrophile coupling reaction to synthesize cyclopropanes will be presented. This method uses zinc salts as an electrochemical mediator in an undivided cell with no sacrificial anode. Finally, a nickel-catalyzed cross-coupling with organomanganese reagents will be presented. This reaction allows the formation of C(sp3)-C(sp3) bonds in a stereoselective fashion with good scalability.