Efficient Synthesis of Fluoroalkylated Imidazoles via a Metal-Free Cascade Michael Additon / Azidation / Cycloamination Process

In the presence of KI and (diacetoxyiodo)benzene (PIDA), primary amines bearing an alpha-hydrogen can be efficiently converted to fluoroalkylated imidazoles by reacting with fluoroalkylated alkynes and sodium azide via a cascade Michael addition/azidation/cycloamination process. KI plays a crucial role in this reaction by generating iodine(I) species to promote the cyclization. Substrate scope was explored, and the application of this protocol was demonstrated. Additionally, a plausible reaction mechanism was proposed.