Hypoiodite-Mediated Catalytic Cyclopropanation of Alkenes with Malononitrile
An efficient synthetic procedure for dicyano-cyclopropanation of alkenes using catalytic amounts of molecular iodine as a precatalyst and tert-butyl hydroperoxide (TBHP) as a terminal oxidant under mild conditions has been developed. This catalytic reaction works especially well for the aryl-substituted double bond affording products of cyclopropanation in high yields. A catalytic cycle based on the generated in situ hypoiodite species has been proposed.
Yoshimura, A.; Jones, T. N.; Yusubov, M. S.; Zhdankina, V. V. Hypoiodite-mediated catalytic cyclopropanation of alkenes with malononitrile. Advanced Synthesis and Catalysis, 2014, 356(16), 3336-3340.