Exploring Guanidinium Organocatalysts for Hypoiodite‐Mediated Reactions

Abstract

AbstractThis account describes our recent work on developing guanidinium hypoiodite‐ catalysts for oxidative carbon‐nitrogen and carbon‐carbon bond‐forming reactions. These reactions proceeded smoothly using guanidinium hypoiodite generated in situ by treating 1,3,4,6,7‐hexahydro‐2H‐pyrimido[1,2‐a]pyrimidine hydroiodide salts with an oxidant. In this approach, the ionic interaction and hydrogen bonding ability of the guanidinium cations enable bond‐forming reactions that have been difficult with conventional methods. Enantioselective oxidative carbon‐carbon bond‐forming reaction was also achieved by using a chiral guanidinium organocatalyst.