Reviving an old route to amides

Abstract

Chemists have been using the Schmidt reaction, which transforms aldehydes and ketones into amides, for nearly 100 years. But the reaction has a downside that prevents it from being widely used: it requires azides, which can be volatile, toxic, and explosive. Ning Jiao and colleagues at Peking University discovered they could replace these dangerous azides with the common industrial solvent nitromethane in a Schmidt-like transformation. Amides made in this manner could be used as drugs, agrochemicals, or commodity chemicals. “Jiao and colleagues have found a way of making an incredibly useful reaction—the insertion of a single nitrogen atom in between two carbons—into a safer and more accessible process,” says Jeffrey Bode, a chemist at the Swiss Federal Institute of Technology (ETH), Zurich, who studies organic synthesis. “The classic approach to synthesizing amides is centered on the activation of carboxylic acids using exotic reagents to enable nucleophilic substitution,” Jiao explains. The