ERROR 1
ERROR 1
ERROR 2
ERROR 2
ERROR 2
ERROR 2
ERROR 2
Password and Confirm password must match.
If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)
ERROR 2
ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.
Olefins are important components in many organic compounds, such as fragrances, natural products, and drugs. And while chemists have many ways of introducing double bonds into molecules, most rely on chemistry developed more than 30 years ago. Researchers led by Phil S. Baran of Scripps Research Institute California have now come up with a new way to introduce olefins into organic compounds (Nature 2017, DOI: 10.1038/nature22307). The reaction—known as decarboxylative alkenylation—starts with ubiquitous alkyl carboxylic acids. The chemists first transform the carboxylic acid into a redox-active ester, which then undergoes nucleophilic attack from an alkenyl zinc reagent in the presence of a nickel or iron catalyst. The whole process takes place in a single pot and can be used to make mono-, di-, tri-, and tetrasubstituted olefins. The reaction also allows exquisite control of olefin geometry because it is established by the geometry of the alkenyl zinc reagent rather than the C–C bond-forming event, as is the case in olefin metathesis. The chemists used the new reaction to prepare more than 60 different olefins, including the prostaglandin (+)-PFG2α (shown; red bonds made via decarboxylative alkenylation).
Join the conversation
Contact the reporter
Submit a Letter to the Editor for publication
Engage with us on X