Friday, April 16 at 4:00pmVirtual Event
“Alkenes as Universal Synthetic Building Blocks”
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 alkene difunctionalization reactions, thereby introducing two new functional groups at each of the alkenyl carbon
atoms. The products formed from these transformations conveniently map onto molecules that are of academic and industrial importance, including many widely used pharmaceutical agents. Our central hypothesis is that coordination of a π-Lewis acidic metal, such as palladium(II), to the
alkene will promote attack of a nucleophile and that the resultant organometallic species can be trapped with an electrophile to furnish the desired 1,2-difunctionalized product. This latter operation involves a
high-oxidation-state intermediate, from which selective reductive elimination can be achieved. In the overall net transformation, one of the two new functional groups is introduced in the form of a nucleophile,
and the other in the form of an electrophile. Lewis basic groups on the substrate are used to coordinate to the metal catalysts, controlling the site-selectivity and suppressing side reactions. These concepts have
been used to invent a series of useful reactions, such as three-component alkene carboamination, where an amino group and an aryl/alkyl/alkenyl group are selectively added across an alkene.
Biography: Keary Engle was born in Lansing and grew up in Holland, MI. His passion for STEM subjects was cultivated in the basement classrooms of Dimnent Chapel, where he participated in the PATH program, while
attending West Ottawa High School. Keary went on to graduate Phi Beta Kappa and summa cum laude from the University of Michigan, earning a B.S. in Chemistry, Economics, Mathematics, and Statistics. His undergraduate research focused on molecular self-assembly, and he first became fascinated by transition metal catalysis during
research abroad experiences at the University of Stuttgart (DAAD RISE Fellow), the Max-Planck-Institute für Kohlenforschung (Fulbright Scholarship), and the University of Stockholm (IDECAT Exchange Fellow). Keary completed a Ph.D. in Chemistry at the Scripps Research Institute and a D.Phil. in Biochemistry at the University of Oxford, during which time he was an NSF Graduate Research Fellow and NDSEGnFellow. Following an NIH Postdoc Fellowship in the laboratory of Nobel Laureaten Robert H. Grubbs at Caltech, Keary joined the Department of Chemistry at Scripps
Research as an Assistant Professor in the summer of 2015 and was promoted to full Professor in 2020. His research interests lie at the interface of organometallic chemistry, organic synthesis, and catalysis. Outside of the lab, Keary enjoys running long distances, eating fried chicken, drinking good beer, and spending time with his wife, son, and fur daughter.