Zhiqi He et al, Aminodealkenylation: Ozonolysis and copper catalysis convert C(sp 3 )–C(sp 2 ) bonds to C(sp 3 )–N bonds, Science (2023).

Editor's summary
Reactions that form carbon–nitrogen bonds most often target carbon centers that are either single bonded to a halogen or double bonded to oxygen or another carbon. He et al. present an alternative sequence that targets a carbon–carbon single bond adjacent to an olefin. Treatment of the allylic carbon compound with ozone followed by copper catalysis formally displaces the pendant olefin with an amine. The reaction can introduce nitrogen into a wide variety of complex terpenes, among other compounds.

Key takeaways

* UCLA researchers have devised a way to produce chemicals used in medicine and agriculture for a fraction of the usual cost.
* Using oxygen as a reagent and copper as a catalyst to break organic molecules' carbon-carbon bonds and convert them into amines, which are widely used in pharmaceuticals.
* Traditional metal catalysis uses expensive metals such as platinum, silver, gold and palladium, but the researchers used oxygen and copper — an abundant base metal.

One chemical used in some anti-cancer drugs, for example, costs pharmaceutical companies $3,200 per gram — 50 times more than a gram of gold. The UCLA researchers devised an inexpensive way to produce this drug molecule from a chemical costing just $3 per gram. They were also able to apply the process to produce many other chemicals used in medicine and agriculture for a fraction of the usual cost.