Science 327, 566–571 (2010)

Many organic molecules are made up of multiple methylene units (–CH2–) in which the carbon–hydrogen bonds are inert to most reagents. Selectively converting just one of these methylenes into something else — to build a drug molecule, for example — is one of the biggest challenges in organic chemistry.

Mark Chen and Christina White at the University of Illinois at Urbana-Champaign have now developed an iron-based catalyst that can help hydrogen peroxide to oxidize specific methylene groups in a predictable manner, mimicking the actions of natural iron-containing enzymes. This process turns methylene into an oxygen-containing chemical group, which can be modified further in subsequent reactions.

The researchers demonstrated their technique on a series of terpenoids, the largest and most diverse set of naturally occurring organic compounds.