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.
Chemists have developed an array of chemical tools that rely on reactive carbon-carbon π bonds or on polar bonds in which charge is unevenly shared between the atoms to drive the formation of new carbon-carbon bonds. Yet methods that act on challenging, nonpolar carbon-carbon bonds are few. Researchers led by Masahiro Murakami of Kyoto University have expanded the synthetic options by demonstrating the efficient exchange of two low-polarity σ bonds in a cross-metathesis-type reaction catalyzed by a palladium isocyanide complex (J. Am. Chem. Soc. 2017 DOI: 10.1021/jacs.7b07667). The method regioselectively opens the four-membered rings of benzocyclobutenone and silacyclobutane and exchanges C(aryl)–C(carbonyl) and C(sp3)–Si bonds to create C(aryl)–Si and C(carbonyl)–C(sp3) bonds and form an eight-membered-ring product. “The work provides a striking demonstration of how metallacycles derived from C–C bond activation can be used to access challenging medium-ring systems,” comments the University of Bristol’s John Bower. “These results suggest that a range of σ-bond-metathesis-based cycloadditions might be achievable by metal-catalyzed union of strained rings.”
Join the conversation
Contact the reporter
Submit a Letter to the Editor for publication
Engage with us on Twitter