Event
Inorganic Chemistry Seminar, Dr. Caleb D. Martin, Baylor University
Inquiries please contact Rosa M. Vargas rvargas@sas.upenn.edu
"Anti-Aromatic Boroles as Reagents for Heterocycle Synthesis"
Our group has been investigating the chemistry of boroles, unsaturated BC4 heterocycles, to access larger unsaturated boracycles.1 The anti-aromatic boroles readily insert atoms and molecular fragments to generate 1,2-azaborine, 1,2-phoaphaborine, 1,2-oxaborine, and 1,2-thiaborine heteroarenes2 which have different properties to their six-membered carbonaceous counterpart, benzene.3 Ongoing efforts are focused on enhancing the electronic properties of these boracycles to explore their utility in electronic materials and pharmaceuticals. Our strategy for the former is to extend conjugation in the inorganic/organic hybrid arenes by utilizing borole-based starting materials with conjugation installed.4 The mechanisms of these reactions and properties of the boracycles will be discussed.
1. Barnard, J. H.; Yruegas, S.; Huang, K.; Martin, C. D. Chem. Commun., 2016, 52, 9985.
2. a) Couchman, S. A.; Thompson, T. K.; Wilson, D. J. D.; Dutton, J. L.; Martin, C. D. Chem. Commun., 2014, 50, 11724. b) Barnard, J. H.; Brown, P. A.; Shuford, K. L.; Martin, C. D. Angew. Chem. Int. Ed., 2015, 54, 12083. c) Yruegas, S.; Patterson, D. C., Martin, C. D. Chem. Commun., 2016, 52, 11724. d) Yruegas, S.; Martin, C. D. Chem. –Eur. J., 2016, 22, 18358.
3. Brown, P. A.; Martin, C. D.; Shuford, K. L. Phys. Chem. Chem. Phys., DOI:10.1039/C9CP02387A.
4. a) Yruegas, S.; Martinez, J. J.; Martin, C.D. Chem. Commun., 2018, 54, 6808. b) Yruegas, S.; Axtell, J. C.; Kirlikovali, K. O.; Spokoyny, A. M.; Martin, C.D. Chem. Commun., 2019, 56, 2892.