Event time:
February 27, 2023 - 4:00pm to 5:30pm
Location:
Sterling Chemistry Laboratory (SCL)
Event description:
Location: SCL 160
Join Yale Chemistry for an Inorganic Chemistry Seminar with Isaac Garcia-Bosch, Professor of Chemistry at Carnegie Mellon University.
Abstract: Our research lab takes inspiration from metalloenzymes to develop metal complexes able to catalyze organic transformations under environmentally benign conditions using cheap reagents such as Cu, and green oxidants such as O2 or H2O2 (Chem. Rev. 2019, 119, 2954.). In 2016, we reported a practical synthetic protocol to oxidize strong C-H bonds with H2O2 using catalytic amounts of Cu and commercially available ligands (Angew. Chem., Int. Ed. 2016, 55, 12873). A detailed mechanistic study revealed that the oxidations occurred via formation of non-selective Fenton oxidants (·OH and ·OOH radicals) that were generated in the LCuII/LCuIII redox cycle. In organic synthesis, an elegant way to overcome the selectivity issues associated with the formation of radicals is the use of directing groups. In this research seminar, we will discuss our findings on the intramolecular hydroxylation of sp2 and sp3 C-H bonds using Cu, directing groups and H2O2 (see J. Org. Chem. 2017, 82, 7887; Inorg. Chem. 2019, 58, 7584, J. Inorg. Biochem. 2021, 223, 111557; and Eur. J. Org. Chem. 2021, 2021, 4536). An alternative approach to avoid the formation of radical species in 3d metal-catalyzed organic synthesis is the use of redox-active ligands. During this seminar, we will also discuss our work on Cu complexes bearing redox-active ligands with tunable H-bonding groups are capable of performing multi-electron multi-proton transformations that mimic the reactivity of Cu-dependent oxidase and peroxidase enzymes (see J. Am. Chem. Soc., 2018, 140, 16625; Chem. Asian. J., 2021, 16, 1608; J. Am. Chem. Soc., 2020, 142, 12265; and J. Am. Chem. Soc., 2022, 144, 16905).
About: Isaac Garcia-Bosch obtained a B.S. in Chemistry at the University of Girona (Catalonia) in 2006. After completing his Ph.D. at the same university, with Prof. Miquel Costas and Prof. Xavi Ribas (2011), he moved to the Johns Hopkins University (Baltimore) as a Marie Curie IOF Postdoctoral Fellow to work with Prof. Kenneth D. Karlin. In 2015, he started his independent career in the Department of Chemistry at Southern Methodist University (Dallas) as Harold A. Jeskey Endowed Chair in Chemistry - Assistant Professor. In 2021, he joined the faculty of the Department of Chemistry at Carnegie Mellon University as Associate Professor.
This seminar is generously sponsored by the Mrs. Hepsa Ely Silliman Memorial Fund