Many of the C–H bonds in hydrocarbons look alike to chemical reagents. As a result, synthetic chemists often have to install activating or directing groups to get reactions to occur at C–H bonds of their choosing.
In a new reaction, a nickel catalyst walks along hydrocarbon chains to activate specific C–H bonds for reaction, without the need for preinstalled activating or directing groups (Nature 2017, DOI: 10.1038/nature22316).
The method, developed by Rubén Martín of the Institute of Chemical Research of Catalonia and coworkers, provides a new route to fatty acids, which are used industrially to make soaps, detergents, rubber, plastics, and dyes. Each reaction produces a single-isomer fatty acid by adding CO2 to a specific C–H bond in a pure alkane or an alkene mixture derived from inexpensive petroleum feedstocks.