A novel strategy was developed for the synthesis of cyclopropane using the I₂/tert-butyl hydroperoxide (TBHP) catalytic system in an alkaline environment. The active methylene compounds, such as cyanoamide and styrene or 1,4-naph- thoquinone were utilized as substrates, and thereby a series of diverse cyclopropane compounds were synthesized in good yields with the absence of column chromatography steps. This approach only required catalytic amount of iodine under transition metal-free conditions, which exhibited the merits of simplicity and readily available starting materials, green and mild reaction conditions, simple post-treatment operations as well as high atom economy. This strategy is expected to provide an innovative route for the facile and efficient green synthesis of cyclopropane derivatives.

Key words: cyclopropane, transition-metal-free, iodine, cyclopropanation