Research published in early 2022 by scientists in the lab of professor M. Christina White, William H. and Janet G. Lycan Professor of Chemistry, was highlighted by Chemical & Engineering News as a "snythesis showstopper" in an end-of-year review of highlights and trends in chemistry in 2022.
"Mixing electron-hungry metal catalysts with electron-rich amines typically kills the catalysts, so metal reagents can’t be used to build tertiary amines from secondary amines. M. Christina White and colleagues at the University of Illinois Urbana-Champaign realized they could get around this problem if they added some salty seasoning to their reactant recipe. By transforming secondary amines into ammonium salts, the chemists found they could react these compounds with terminal olefins, an oxidant, and a palladium sulfoxide catalyst to create myriad tertiary amines with a variety of functional groups (example shown). The chemists used the reaction to make the antipsychotic drugs Abilify and Semap and to transform existing drugs that are secondary amines, such as the antidepressant Prozac, into tertiary amines, demonstrating how chemists might make new drugs out of existing ones (Science 2022, DOI: 10.1126/science.abn8382)." — C&EN's Year in Chemistry 2022
Read more about this research project that included current graduate students Brenna Budaitis and Devon Fontaine and former PhD student Siraj Ali, who is now a postdoctoral researcher at M.I.T. in Boston.