Chemistry Department Faculty
Shih-Yuan Liu
Professor of Chemistry
Shih-Yuan Liu
Ph.D.
Contact
Merkert Center 334
Telephone: 617-552-8543
Email: shihyuan.liu@bc.edu
ORCID 0000-0003-3148-9147
Education
- B.S., Vienna University of Technology
- Ph.D., Massachusetts Institute of Technology
Research Interests
Development of boron(B)-nitrogen(N)-containing heterocycles, specifically azaborines.
Research
We are engaged in synthetic chemistry with emphasis on developing molecules of importance in biomedical research and materials science.
We are interested in the development of boron(B)-nitrogen(N)-containing heterocycles, specifically azaborines. These are structures resulting from the replacement of two carbon atoms in benzene with a boron and a nitrogen atom. Azaborines are isosteres of the important family of benzenoid compounds / arenes. We aim to exploit the unique properties of azaborines and investigate their potential as arene surrogates in materials and biomedical research. Our approach combines the broad utility of arenes with the unique elemental features of boron. Areas of exploration include organic synthesis, catalysis, hydrogen storage, optoelectronic materials, and drug discovery. The development of azaborines has the potential of changing the way chemists think about creating molecular diversity, namely through isosterism.
Representative Key Publications
- Marwitz, A. J. V.; Matus, M. H.; Zakharov, L. N.; Dixon, D. A.; Liu, S.-Y. "A Hybrid Organic/Inorganic Benzene" Angew. Chem. Int. Ed. 2009, 48, 973-977. [10.1002/anie.200805554]
- Abbey, E. R.; Zakharov, L. N.; Liu, S.-Y. "Boron in Disguise: The Parent "Fused" BN Indole" J. Am. Chem. Soc. 2011, 133, 11508-11511. [10.1021/ja205779b]
- Ishibashi, J. S. A.; Marshall, J. L.; Maziere, A.; Lovinger, G. J.; Li, B.; Zakharov, L. N.; Dargelos, A.; Graciaa, A.; Chrostowska, A.; Liu, S.-Y. “Two BN Isosteres of Anthracene: Synthesis and Characterization” J. Am. Chem. Soc. 2014, 136, 15414-15421. [10.1021/ja508813v]
- Xu, S.; Zhang, Y.; Li, B.; Liu, S.-Y. “Site- and Stereo-selective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex" J. Am. Chem. Soc. 2016, 138, 14566-14569. [10.1021/jacs.6b09759]
- Zhao, P.; Nettleton, D. O.; Karki, R.; Zecri, F. J.; Liu, S.-Y. “Medicinal Chemistry Profiling of Monocyclic 1,2-Azaborines" ChemMedChem 2017, 12, 358-361. [10.1002/cmdc.201700047]
- Boknevitz, K.; Italia, J. S.; Li, B.; Chatterjee, A.; Liu, S.-Y. "Synthesis and Characterization of an Unnatural Boron and Nitrogen-containing Tryptophan Analogue and its Incorporation into Proteins" Chem. Sci. 2019, 10, 4994-4998. [10.1039/C8SC05167D]