NIU Department of
Chemistry & Biochemistry
Where the study of matter...matters!
Associate Professor
Office: Faraday Hall 336
Phone: (815) 753-6841
qyao@niu.edu
Research Associate, Columbia University, 1996-1998
Ph.D., University of Illinois at Chicago, 1996
M.S., Shanxi University, 1988
B.S., Shanxi Medical College, 1983
Organic synthesis and synthetic methodology; new transition metal-catalyzed/mediated reactions; green chemistry; free radical chemistry; combinatorial chemistry.
A SeCSe–Pd(II) pincer complex as a highly efficient catalyst for allylation of aldehydes with allyltributyltin. Yao, Q.; Sheets, M. (2006) J. Org. Chem., 71: 5384–5387.
An ionic liquid-tagged second generation Hoveyda–Grubbs ruthenium carbene complex as highly reactive and recyclable catalyst for ring-closing metathesis of di-, tri- and tetrasubstituted dienes. Yao, Q.; Sheets, M. (2005) J. Organomet. Chem., 690: 3577–3584.
Poly(fluoroalkyl acrylate)-bound ruthenium carbene complex: A fluorous and recyclable catalyst for ring-closing olefin metathesis. Yao, Q.; Zhang, Y. (2004) J. Am. Chem. Soc., 126: 74–75.
Selenium-ligated palladium(II) complexes as highly active catalysts for carbon–carbon coupling reactions: The Heck reaction. Yao, Q.; Kinney, E. P.; Zheng, C. (2004) Org. Lett., 6: 2997–2999.
Immobilization of the Grubbs second-generation ruthenium–carbene complex on poly(ethylene glycol): A highly reactive and recyclable catalyst for ring-closing and cross metathesis. Yao, Q.; Motta, A. R. (2004) Tetrahedron Lett., 45: 2447–2451.
Ligand-free Heck reaction: Pd(OAc)2 as an active catalyst revisited. Yao, Q.; Kinney, E. P.; Yang, Z. (2003) J. Org. Chem., 68: 7528-7531.
Olefin metathesis in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate using a recyclable Ru catalyst: Remarkable effect of a designer ionic tag. Yao, Q.; Zhang, Y. (2003) Angew. Chem. Int. Ed. Engl., 42: 3395-3398.
OsO4 in ionic liquid [Bmim]PF6: A recyclable and reusable catalyst system for olefin dehydroxylation. Remarkable effect of DMAP. Yao, Q. (2002) Org. Lett., 4: 2197-2199.
Research in my laboratory focuses on the development of new synthetic methods for the rapid construction of organic materials of biological importance, and molecules with interesting and useful properties. Generally, new catalytic systems are first designed and their performance evaluated. This is followed by in-depth investigation of their application in organic synthesis. Particular emphasis is given to those catalyst systems that show unusual efficiency and atom economy, as illustrated by the examples shown below.
Currently we are also interested in the heterogenization of some of the most powerful homogeneous catalysts, with a view to making them easy to separate and re-use while retaining catalytic efficiency. Toward this end, soluble supports such as an ionic liquid, poly(ethylene glycol), or fluorous polymers are used as platforms for anchoring the catalysts, as exemplified by the recyclable and reusable catalysts for olefin metathesis shown in the two diagrams below.
This air-stable, fluorous polymer-bound Ru catalyst effects the ring-closing metathesis of a broad spectrum of diene and enyne substrates in minimally fluorous solvent systems with high reactivity. The catalyst can be readily separated by fluorous extraction and reused for up to 20 cycles with minimal loss of efficiency.
The ruthenium carbene complex 1, bearing a designer ionic tag, is a highly reactive catalyst for the ring-closing metathesis of various diene and enyne substrates in minimally ionic solvent systems. The catalyst can be recycled and reused for up to 10 cycles without significant loss of activity.