Keary M. Engle, PhD, Professor of Chemistry The Scripps Research Institute

Title of talk: Metal–olefin interactions and the catalytic chemistry they inspire

Abstract: Alkenes are inexpensive, widely available chemical feedstocks that can be sourced from petroleum or renewable resources. The goal of research in the Engle lab is to develop novel catalytic alkene functionalization reactions that introduce new functional groups at each of the alkenyl carbon atoms in a programmable fashion. In this way, simple planar starting materials can be directly converted into densely functionalized, stereochemically defined products, which can then serve as building blocks for structurally complex target molecules that are of academic and industrial importance, including many widely used pharmaceutical agents. To this end, the Engle lab has developed strategies involving directing auxiliaries, native directing groups, and transient directing groups, as well as complementary non-directed approaches that are compatible with a variety of metals, redox manifolds, and coupling partners. Detailed mechanistic studies have shed light on the interplay between the substrate, metal, and ancillary ligands in dictating reaction outcomes, informing new catalyst designs through an iterative feedback loop.

Bio: Keary grew up in Holland, MI, and graduated as Salutatorian from West Ottawa High School (WOHS) in 2003. His interest in STEM was first sparked by participation in the Program for the Academically Talented at Hope College (PATH) and the West Ottawa Science Olympiad Team coached by Bob Myers and the late Gus Lukow.

Keary went on to graduate Phi Beta Kappa and summa cum laude from the University of Michigan in 2007, where he carried out research in the laboratory of Prof. Adam J. Matzger under the mentorship of Katherine Plass (now a faculty member at Frankin & Marshall College) characterizing self-assembled physisorbed monolayers using scanning tunneling microscopy. During undergrad, he spent one summer studying gold catalysis with Prof. A. Stephen K. Hashmi at the University of Stuttgart as a DAAD RISE Fellow, and then spent the year after graduation performing research with Prof. Manfred T. Reetz at the Max-Planck-Institut für Kohlenforschung as a Fulbright Scholar and with Prof. Jan E. Bäckvall at Stockholm University as an IDECAT Exchange Fellow. As a Skaggs-Oxford Scholar, NSF Graduate Research Fellow, and NDSEG Fellow, Keary completed his doctoral research jointly at The Scripps Research Institute with Prof. Jin-Quan Yu and the University of Oxford with Profs. Véronique Gouverneur and John M. Brown, earning a PhD in Chemistry and a DPhil in Biochemistry in 2017. During grad school, he also carried out summer research with Prof. Kyoko Nozaki at the University of Tokyo as an NSF/JSPS EASPI Fellow. His thesis research identified mono-N-protected amino acids (MPAAs) as ligands that accelerate C–H bond cleavage in palladium(II) catalysis and elucidated the effects of hydrogen bonding on the nucleophilic reactivity of fluoride, contributions that were recognized with the 2014 IUPAC-Solvay International Award for Young Chemists.

After completing a two-year appointment as an NIH Postdoctoral Fellow at Caltech with the late Prof. Robert H. Grubbs developing new olefin metathesis catalysts, Keary joined the Department of Chemistry at Scripps Research as an Assistant Professor in the summer of 2015. In 2020, he was promoted to full Professor with tenure. His research interests lie at the interface of organometallic chemistry, organic synthesis, and catalysis. In particular, the Engle lab has invented general and versatile strategies for the programmed functionalization of olefins and developed nickel and palladium catalysts that are widely used in academic and industrial research labs around the world.

Outside of the lab, Keary enjoys running (ultra)marathons, eating fried chicken, and spending time with his wife, son, and fur children (Hermione and Kingsley).