1st Diploma, Vienna University of Technology, 1997. Ph.D., Massachusetts Institute of Technology, 2003 (Gregory C. Fu). Postdoctoral: Massachusetts Institute of Technology, 2003-06 (Daniel G. Nocera). At Oregon since 2006.

Research Interests

We are engaged in synthetic organic/organometallic chemistry with emphasis on developing molecules of importance in biomedical research and materials science.

1) We are interested in the development of B–N-containing heterocycles, namely 1,2-dihydro-1,2-azaborines. These are structures that are isoelectronic and isostructural to benzene. Benzene, the epitome of aromatic compounds, has played a pivotal role in our fundamental understanding of the concept of aromaticity. In addition to this educational value, the chemistry and applications of benzene derivatives have become ubiquitous in our daily lives (e.g., plastics, drugs, etc.).

We aim to exploit the unique properties of 1,2-dihydro-1,2-azaborines and investigate their potential as benzene 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, optoelectronic materials, catalysis, drug discovery, and cancer therapy. The development of 1,2-dihydro-1,2-azaborines has also the potential of changing the way chemists think about creating molecular diversity, namely through isosterism.

2) We are investigating rearrangement-based methodologies for the synthesis of arene and carbocyclic nucleoside derivatives. These classes of molecules play important roles in organic and pharmaceutical chemistry. The salient feature of our method is that both families of molecules can be generated from a single common structural motif depending on the judicious choice of reaction parameters. Our studies have unraveled the dichotomy of this interesting rearrangement process, and we are pursuing the application of our methodology to the synthesis biologically active molecules.

We are skilled in a variety of experimental techniques commonly applied in synthetic organic/organometallic chemistry, e.g., air-free Schlenk line and glovebox techniques for the preparation of our compounds, and X-Ray, NMR, MS, IR, UV-vis, HPLC, GC, electrochemistry for their characterization.

Publications:

Mascarenhas, C. M.; Duffey, M. O.; Liu, S.-Y.; Morken, J. P. “Simple Metal Alkoxides as Effective Catalysts for the Hetero-Aldol-Tishchenko Reaction” Org. Lett. 1999, 1, 1247-
1249.

Liu, S.-Y.; Choi, M. J.; Fu, G.C. “A Surprisingly Mild and Versatile Method for Palladium-Catalyzed Suzuki Cross-Couplings of Aryl Chlorides in the Presence of a Triarylphosphine” Chem. Commun. 2001, 2408 2409.

Liu, S.-Y.; Lo, M. M.-C.; Fu, G. C. “1,2-Azaborolyls, Isoelectronic Analogues of the Ubiquitous Cyclopentadienyl Ligand: The First Synthesis of B-Heteroatom-Substituted 1,2-Azaborolyl Complexes and an Assessment of their Electronic Features” Angew. Chem. Int. Ed. 2002, 41, 174-176.

Liu, S.-Y.; Hills, I.D.; Fu, G. C. “The First General Method for the Synthesis of Transition Metal p Complexes of an Electronically Diverse Family of 1,2-Azaborolyls” Organometallics 2002, 21, 4323-4325.

Liu, S.-Y.; Nocera, D. G. “Hangman Salophens” J. Am. Chem. Soc. 2005, 127, 5278-5279.

Liu, S.-Y.; Hills, I. D.; Fu, G. C. “Synthesis, Resolution, and Aldol Reactions of a Planar-Chiral Lewis Acid Complex” J. Am. Chem. Soc. 2005, 127, 15352-15353.

Liu, S.-Y.; Nocera, D. G. “A Simple and Versatile Method for Alkene Epoxidation using Aqueous H2O2 and Manganese Salophen Catalysts” Tetrahedron Lett. 2006, 47, 1923-1926.

Liu, S.-Y.; Lo, M. M.-C.; Fu, G. C. “The Synthesis of an Enantiopure Planar-Chiral Lewis Acid Complex via Kinetic Resolution and its Application in Stereoselective Additions to Imines” Tetrahedron 2006, 62, 11343-11349.

Liu, S.-Y.; Soper, J. D.; Yang, J. Y.; Rybak-Akimova, E. V.; Nocera, D. G. “Mechanistic Studies of Hangman Salophen-Mediated Activation of O—O Bonds” Inorg. Chem. 2006, 45, 7572-7574.

Marwitz, A. J. V.; Abbey, E. R.; Jenkins, J. T.; Zakharov, L. N.; Liu, S.-Y.* “Diversity through Isosterism: The Case of Boron-Substituted 1,2-Dihydro-1,2-azaborines” Org. Lett. 2007, 9, 4905-4908.

Abbey, E. R.; Zakharov, L. N.; Liu, S.-Y.* “Crystal Clear Structural Evidence for Electron Delocalization in 1,2-Dihydro-1,2-azaborines” J. Am. Chem. Soc. 2008, 130, 7250-7252.
Highlighted in Chemical & Engineering News (C&EN) (2008, June 16, page 12).

To Contact Dr. Liu:
lsy@uoregon.edu

WEBMASTER
chem@uoregon.edu