Cyclopropanation of alkenes is an important chemical transformation that leads to a cyclic system commonly found in natural products, bioactive molecules, and intermediates of medicinal compounds. Synthetic procedures of cyclopropanation from alkenes using hypervalent iodine reagents are known. Most procedures of cyclopropanations using stoichiometric reagent are performed under harsh conditions or require environmentally unsafe transition metal catalyst, and thus the development of new procedure for cyclopropanations of alkenes is desirable. Herein, we disclose the hypoiodite mediated stoichometric or catalytic cyclopropanation of alkenes using iodine sources and suitable oxidants. In the case of stoichometric reaction, in the presence of LiI (1.5 equiv) and <i>t</i>BuOCl (1.5 equiv) in the reaction mixture, cyclopropanations of malononitrile with alkenes proceeded efficiently, and we obtained desired cyclopropanes in generally good yields. Also, the catalytic cyclopropanation using I<sub>2</sub> (20 mol%) and TBHP as oxidant gave the desired products in good yields (up to 96%).

Hypoiodite mediated stoichometric or catalytic cyclopropanation of alkenes with malononitrile

249th National Meeting (2015)

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