The ‘radical carbenoid’, discovered by Dr. Suero and his group, allows stereoconvergent cyclopropanation reaction.
To day, chemists synthesize cyclopropanes using pure E or Z alkenes as starting materials and usually, dangerous, unstable reagents such as diazomethane or iodomethylzinc iodide. Now, a team of researchers in Dr. Suero’s group designed a new strategy that allows the stereoconvergent preparation of trans-cyclopropanes starting from E/Z alkene mixtures. Moreover, this photoredox catalytic method uses diiodomethane –a commercially available, easy to handle reagent– as the methylene source.
This research represents the first example of a stereoconvergent cyclopropanation reaction. It is also the first proposal of a new type of carbenoid species, dubbed ‘radical carbenoid’, theoretically equivalent to a triplet carbene but with a completely unprecedented reactivity.
A Stereoconvergent Cyclopropanation Reaction of Styrenes
A. M. del Hoyo, A. G. Herraiz and M. G. Suero.
Angewandte Chemie, International Edition, 2016, DOI: