Friday, January 14 at 4:00pm to 5:00pm
A. Paul Schaap Science Center, Auditorium 1000
35 East 12th Street, Holland, MI 49423-3605
Professor Jennifer M. Schomaker, University of Wisconsin-Madison
Taming nitrene reactivity with silver catalysts
Abstract: Over 80% of the pharmaceuticals currently on the market contain at least one carbon-nitrogen bond, as do many important biomolecules. Thus, methods that enable chemists to introduce nitrogen into a broad range of hydrocarbon feedstocks in an efficient, atom-economical, and environmentally friendly manner is of intense interest to the community. In particular, the prevalence of carbon-hydrogen bonds in organic molecules make them ideal targets for functionalization to furnish more valuable compounds. However, achieving this goal presents a number of challenges, including the strength and relative inertness of the C–H bond, the sheer number of C–H bonds present in many convenient building blocks, and the difficulty of targeting a specific site for installation of a new C–N bond. In this talk, I describe our group’s efforts to harness unusual features of silver coordination complexes to catalyze nitrene transfer reactions capable of transforming specific C–H bonds to C–N bonds in a tunable manner. Selected design principles underlying the ability to alter the chemo-, site-, and stereoselectivity of C–H bond amidations will be presented and examples for the late-stage functionalization of medicinally relevant molecules highlighted.
Ju, M.; Schomaker, J. M. Nature Rev. Chem. 2021, 5, 580-594.
Zerull, E.; Vine, L.; Schomaker, J. M. Synlett 2020, 32, 7-13.
Ju, M.; Zerull, E.; Roberts, J.; Huang, M.; Guzei, I.; Schomaker, J. M. J. Am. Chem. Soc. 2020, 142, 12930–12936.
Ju, M.; Huang, M., Vine, L.; Roberts, J.; Dehghany, M.; Schomaker, J. M. Nature Catal. 2019, 2, 899-908.
Huang, M.; Yang, T.; Paretsky, J.; Berry, J.; Schomaker, J. M. J. Am. Chem. Soc. 2017, 139, 17376-17386.
Ju, M.; Weatherly, C.; Guzei, I.; Schomaker, J. M. Angew. Chem. Int. Ed. 2017, 56, 9944-9948.
Alderson, J.; Corbin, J. R.; Schomaker, J. M. Accts. Chem. Res. 2017, 50, 2147-2158.
Weatherly, C. D.; Alderson, J.; Berry, J. F.; Hein, J. E.; Schomaker, J. M. Organometallics 2017, 36, 1649–1661.
Dolan, N.; Scamp, R. J.; Yang, T.; Berry, J.; Schomaker, J. M. J. Am. Chem. Soc. 2016, 138, 14658.
Scamp, R.; Alderson, J.; Phelps, A. M.; Dolan, N. S.; Schomaker, J. M. J. Am. Chem. Soc. 2014, 136, 16720.
Rigoli, J. W.; Weatherly, C. D.; Alderson, J.; Vo, B. T.; Schomaker, J. M. J. Am. Chem. Soc. 2013, 135, 17238.
Professor Schomaker began her research career as an undergraduate intern at Dow Chemical in Organic Chemicals and Polymers, later moving to Agricultural Chemicals Process Research, where she participated in the route selection and scale-up campaigns for two new herbicides. She obtained her Ph.D. with Professor Babak Borhan at Michigan State University in 2006 before moving to UC-Berkeley as an NIH postdoctoral fellow in the labs of Professor Robert G. Bergman and F. Dean Toste. She began her independent career at the University of Wisconsin-Madison in 2009, where she is now a full professor.