09/28/17 -9:45 AM to 11:00 AM
Department Seminar: Professor Daniel J. Weix
"Cross-Electrophile Coupling: Principles and New Reactions"
Cross-electrophile coupling is the broadly-defined union of two different electrophiles through transition-metal catalysis under reducing conditions. By avoiding pre-formed carbon nucleophiles, cross-electrophile coupling avoids the challenges of substrate availability and functional group compatibility associated with these organometallic reagents. Substitution of a second electrophile for the organometallic partner in cross-couplings offers the potential to dramatically increase the number and types of molecules that can be easily made because of the large number of commercially available carbon electrophiles (>1 million R-X vs. ~5 thousand R-B(OH)2) and the low cost of all components. We have demonstrated reactions that couple organic halides with enones, aryl halides with alkyl halides, acid chlorides and thioesters with alkyl halides, and aryl halides with aryl triflates. Along the way, we have demonstrated their high functional-group compatibility and shed light on why certain reactions are cross-selective and others are not. This talk will introduce our current understanding of the origin of selectivity in cross-electrophile coupling reactions, introduce the use of cooperative catalysis, and show how these concepts can be used to further expand the scope of cross-electrophile coupling.
Professor Weix is the Wayland Noland Distinguished Chair of Chemistry at the University of Wisconsin-Madison. He graduated from Columbia University in 2000, where he conducted research on helicenes with Thomas Katz. During his doctorate work with Jonathan Ellman at the University of California (2000-2005), he worked on improved methods for the synthesis and the use of tert-butanesulfinamide. Following post-doctoral work on Ir-catalyzed allylation chemistry with John Hartwig, Weix began his independent career at the University of Rochester in 2008 and, in 2017, moved to the University of Wisconsin. He has been the recipient of a National Science Foundation pre-doctoral fellowship, a National Institutes of Health post-doctoral fellowship, Green Chemistry awards from Pfizer-Groton, a Thieme Journal Award, an Alfred P. Sloan Research Fellowship, a Camille Dreyfus Teacher-Scholar Award, the Novartis Early Career Award, a Japan Society for the Promotion of Science Research Fellowship, and was recently elected a fellow of the American Association for the Advancement of Science. His research program is currently supported by the NIH, the ACS PRF, Novartis, Boehringer-Ingelheim, Eli Lilly, and Pfizer.