Pinning aryl groups on alkanes

Abstract

Unactivated alkanes are difficult to functionalize, and most catalysts that derivatize them by opening hydrocarbon C–H bonds are based on precious transition metals. Researchers have now developed a class of intermolecular C–H arylation reactions that use catalysts made from more-abundant materials: silicon and boron. The reaction adds aryl groups to C–H bonds of simple hydrocarbons, including to the notoriously inert bonds in methane, at mild temperatures (Science 2017, DOI: 10.1126/science.aam7975). “Alkanes are bulk components of gasoline and as such are supercheap commodities, which, if converted to functionalized compounds, would become much more valuable,” comments Jay Siegel of Tianjin University, who developed a related intramolecular reaction but was not involved in the new study. “This is an area rich in prospects, with a bright future for chemical synthetic methods development.” Hosea M. Nelson and coworkers at the University of California, Los Angeles, prepare the new organosilicon catalyst fr...