Efforts to selectively break carbon-hydrogen bonds continue apace.
The decision by Dalibor Sames to withdraw two published papers1,2 and part of a third3 has drawn unwanted attention to the chemical field of C–H functionalization. But the furore seems unlikely to dim the area's lustre.
Sames says in his retraction4 that his group at Columbia University in New York has been unable to reproduce the published results since graduate student and co-author Bengü Sezen left the lab. Sezen stands by the results and says that she is prepared to repeat the work under Sames's supervision. Columbia University, meanwhile, has launched an investigation into the matter.
C–H functionalization — the art of replacing carbon-bound hydrogen atoms in organic molecules with something more interesting — is unlikely to be badly damaged. “There are dozens, even hundreds, of exciting papers published every year,” says Alan Goldman of Rutgers University in Piscataway, New Jersey, author of a recent survey of the field. “I don't think the retractions will cast any shadow.”
Bonds between carbon and hydrogen atoms are ubiquitous in the raw materials from which synthetic chemists make new molecules. Unfortunately, it is a serious headache to cut the strong bond between a particular hydrogen atom and the carbon to which it is attached and replace that hydrogen with something else: another carbon, say, or a phenyl group. Most techniques will indiscriminately break all such bonds in any given molecule.
The work at the Sames lab and elsewhere aims to replace this blunt approach with something more delicate: employing reusable catalysts to fashion reactions targeted at specific bonds. Such selectivity would have practical applications in industrial processes to make pharmaceuticals or fuels.
Chemist Robert Bergman at the University of California, Berkeley, is sanguine about the technique breaking out of the lab. “If you asked people ten years ago whether anyone would ever come up with a catalytic method to do this, they would have said no. I don't think it is outrageous to say that in five or ten years there will be commercial applications.”
“This should have hit the news because it was right and exciting, instead of hitting the news because it was wrong,” laments Travis Williams, a postdoc in the field at Berkeley. “I am sorry that the world is going to think that chemists get it wrong, because, almost always, chemists get it right.”