By Carol Clark
For decades, chemists have aspired to do carefully controlled chemistry on carbon-hydrogen bonds. The challenge is staggering. It requires the power of a miniature wrecking ball to break these extremely strong bonds, combined with the finesse of microscopic tweezers to single out specific C-H bonds among the many crowded onto a molecule.
The journal Nature published a method that combines both these factors to make an inert C-H bond reactive — effectively turning chemical “trash” to “treasure.”
“We can change a cheap and abundant hydrocarbon with limited usefulness into a valuable scaffold for developing new compounds — such as pharmaceuticals and other fine chemicals,” says J.T. Fu, a graduate student at Emory University and first author of the paper.
The Nature paper is the latest in a series from Emory University demonstrating the ability to use a dirhodium catalyst to selectively functionalize C-H bonds in a streamlined manner, while also maintaining virtually full control of the three-dimensional shape of the molecules produced.
“This latest catalyst is so selective that it goes cleanly for just one C-H bond — even though there are several C-H bonds very similar to it within the molecule,” says Huw Davies, Emory professor of organic chemistry and senior author of the paper. “That was a huge surprise, even to us.”
Click here to read more about the discovery.
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