Got to Break it to Make It: Cyclizations, Cycloadditions, and Carbene-mediated Reactions Triggered by C-C, C-O, and C-N Bond Cleavage 


Chemical reactions often require some level of bond activation to proceed forward. Often, this activation occurs through bond cleavage to generate ions or radical species that undergo subsequent bond-forming reactions. Strategic synthetic design enables chemists to take advantage of various modes of bond cleavage to build molecular complexity. With this framework in mind, the France lab has developed various synthetic approaches involving C-C, C-O, and C-N bond cleavage that enable bond formation and rapid structural assembly. Herein, the design principles and implementation of these approaches will be discussed with selected examples highlighting synthetic utility with application in natural product synthesis, medicinal chemistry, process chemistry, and carbohydrate upcycling.