Add Light, Break Rules

Abstract

Small molecules with a carbon-carbon double bond—alkenes—are starting points for chemicals in products such as paints and flavorings. But many ways to modify alkenes are energy intensive or depend on costly metal catalysts. Neither issue plagues new chemistry from a University of North Carolina, Chapel Hill, team. The researchers presented their work at the American Chemical Society’s national meeting in New Orleans. The chemistry is still at an early stage, said David A. Nicewicz, who led the project. Instead of a metal, it uses a pair of organic molecules as the catalyst: a commercially available acridinium salt and 2-phenylmalono­nitrile. Harnessing light from a low-energy 15-W light-emitting diode lamp, the catalyst transforms an alkene into a cation radical. It’s possible to add “a whole slew” of motifs to the alkene from there, Nicewicz said. At a session in the Division of Organic Chemistry, graduate students David S. Hamilton and Tien M. ...