The Chirik Group at the Princeton Department of Chemistry is chipping away at one of the great challenges of metal-catalyzed C–H functionalization with a new method that uses a cobalt catalyst to differentiate between bonds in fluoroarenes, functionalizing them based on their intrinsic electronic properties.
This article has been reviewed according to Science X's editorial process and policies . Editors have highlighted the following attributes while ensuring the content's credibility: This graphic gives a general portrait of the value-added products one can access using this chemistry. Credit: Science (2023). DOI: 10.1126/science.adj6527 In a paper published this week in Science, researchers show they are able to bypass the need for steric control and directing groups to induce cobalt-catalyzed borylation that is meta-selective. The lab's research showcases an innovative approach driven by deep insights into organometallic chemistry that have been at the heart of its mission for over a decade. In this case, the Chirik Lab drilled down into how transition metals break C–H bonds, uncovering a method that could have vast implications for the synthesis of medicines, natural products, and materials. And their method is fast—comparable in speed to those that rely on iridium. The research is outlined in "Kinetic and Thermodynamic Control of C(sp2)–H Activation Enable Site-Selective Borylation," by lead author Jose Roque, a former postdoc in the Chirik Group; postdoc Alex Shimozono; and P.I. Paul Chirik, the Edwards S. Sanford Professor of Chemistry and former lab members Tyler Pabst, Gabriele Hierlmeier, and Paul Peterson. 'Really fast, really selective' "Chemists have been saying for decades, let's turn synthetic chemistry on its head and make the C–H bond a reactive part of the molecule. That would be incredibly important for drug discovery for the pharmaceutical industry or for making materials," said Chirik. "One of the ways we do this is called C–H borylation, in which you turn the C–H bond into something else, into a carbon–boron bond. Turning C–H to C–B is a gateway to great chemistry." Benzene rings are highly represented motifs in medicinal chemistry. However, chemists rely on traditional approaches to functionalize them. The Chirik Group develops new…