People & Research

Michael Rubin

Assistant Professor

Michael Rubin photo University of Kansas
Department of Chemistry
1251 Wescoe Hall Drive
Malott Hall, Room 5088
Lawrence, KS 66045

Phone: (785) 864-5071

Fax: (785) 864-5396

Email: mrubin@ku.edu

Academic Degrees

  • B.Sc., 1994, Moscow State University, Moscow, Russia
  • Ph.D., 1998, The Moscow State University, Moscow, Russia
  • Visiting Research Fellow, 1996, University of Wales, Bangor, UK
  • Visiting Research Fellow, 1997, Université de Paris Sud, Orsay, France
  • Postdoctoral Research Associate, 1999-2003, University of Illinois at Chicago
  • Research Assistant Professor, 2003-2005, University of Illinois at Chicago

Areas of Specialization

Synthetic Methodology, Transition Metal Catalysis, and Physical Organic Chemistry

Research Interests

One of the directions of our research concerns the development of a novel family of chiral ligands employing a rigid cyclopropyl backbone for asymmetric transition metal catalysis. Significant conformational constrains and a well defined geometry make a three-membered carbocycle a unique, light weight, and rigid ligand platform capable of efficient stereo- and regiocontrol. This project integrates synthetic and theoretical approaches and invovles the elaboration of new methodologies towards phosphorous-containing cyclopropanes, synthesis of organometallic complexes, and development of new catalytic processes utilizing novel catalysts.

rubin1

rubin2

Another aspect of this project stems from the fact that some nucleotide mimics possessing a cyclopropyl phosphorous fragment exhibit potent antiviral and antimalarial activities. Accordingly, development of synthetic methodologies towards phosphorous-containing cyclopropanes is also aimed at expanding the pool of versatile cyclopropylphosphonate derivatives available for biological screening and providing additional tools for structure optimization en route to more selective drug candidates.

rubin3

In the frame of a multidisciplinary project initiated by the Center of Environmentally Beneficial Catalysis, our group is involved in the design and development of new, environmentally benign transition metal-catalyzed processes for manufacturing of commodity and specialty chemicals. This includes synthesis and testing of new catalyst systems, optimization of reaction conditions, and adaptation of existing transition metal-catalyzed methodologies to CO2-expanded organic and ionic liquid media. One of the examples of such processes, currently being developed in our laboratories, is the synthesis of non-steroidal anti-inflammatory drugs via the Rh-catalyzed asymmetric hydroformylation and Mn-catalyzed oxidation in aqueous media.

rubin4

rubin5

Selected publications

Rubina, M.; Rubin, M.; Gevorgyan, V.Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes: Stereo- and Regioselective Approach Toward Multisubstituted Cyclopropyl Synthons. J. Am. Chem. Soc. 2002, 124, 11566-11567.

Lewis, F. D.; Zuo, X.; Gevorgyan, V.; Rubin, M. Symmetry-Enforced Conformational Control of Photochemical Reactivity in 2-Vinyl-1,3-terphenyl. J. Am. Chem. Soc. 2002, 124, 13664-13665.

Rubina, M.; Rubin, M.; Gevorgyan, V. Catalytic Enantioselective Hydroboration of Cyclopropenes. J. Am. Chem. Soc. 2003, 125, 7198-7199.

Rubin, M.; Markov, J.; Chuprakov, S.; Wink, D. J.; Gevorgyan, V. Highly Regio-Controlled Pd-Catalyzed Cross-Coupling Reaction of Terminal Alkynes and Allenyl Phosphine Oxides.J. Org. Chem. 2003, 68, 6251-6256.

Rubin, M.; Sromek, A. W.; Gevorgyan, V. New Advances in Selected Transition Metal-Catalyzed Annulations (Account).Synlett 2003, 2265-2291.

Rubin, M.; Gevorgyan, V. Simple Large-Scale Preparation of 3,3-Disubstituted Cyclopropenes. Easy Access to Stereodefined Cyclopropylmetals via Transition Metal-Catalyzed Hydrometalation (Practical Synthetic Procedures).Synthesis 2004, 796-800.

Andreev, A. A.; Konshin, V. V.; Komarov, N. V.; Rubin, M.; Brouwer, C.; Gevorgyan, V. Direct Electrophilic Silylation of Terminal Alkynes.Org. Lett. 2004, 6, 421-424.

Rubina, M.; Rubin, M.; Gevorgyan, V. Catalytic Enantioselective Hydrostannation of Cyclopropenes.J. Am. Chem. Soc. 2004, 126, 3688-3689.

Schwier, T.; Rubin, M.; Gevorgyan, V. B(C6F5)3-Catalyzed Allylation of Propargyl Acetates with Allylsilanes. Org. Lett. 2004, 6, 1999-2001.

Chuprakov, S.; Rubin, M.; Gevorgyan, V. Direct Palladium-Catalyzed Arylation of Cyclopropenes. J. Am. Chem. Soc. 2005, 127, 3714-3715.

Rubin, M.; Trofimov, A.; Gevorgyan, V. Can Polarization of Triple Bond in Tolanes Be Deduced from 13C NMR Shifts? Re-evaluation of Factors Affecting Regiochemistry of the Palladium-Catalyzed Hydrostannation of Alkynes. J. Am. Chem. Soc. 2005, 127, 10243-10249.

Lewis, F. D.; Sajimon, M. C.; Zuo, X.; Rubin, M.; Gevorgyan, V. Competitive 1,2-and 1,5-Hydrogen Shifts Following 2-Vinylbiphenyl Photocyclization. J. Org. Chem. 2005, 70, 10447-10452.

Lewis, F. D.; Crompton, E. M.; Sajimon, M. C.; Rubin, M.; Gevorgyan, V. Ring‑Closing Photoisomerization of Some 2,2-Diarylstyrenes. Photochem. Photobiol. 2006, 82, 119-122.

Lewis, F. D.; Karagiannis, P. C.; Sajimon, M. C.; Lovejoy, K. S.; Zuo, X.; Rubin, M.; Gevorgyan, V. Solvent-Dependent Photocyclization and Photophysics of Some 2-Ethynylbiphenyls. Photochem. Photobiol. Sci. 2006, 82, 369-375.

Rubin, M.; Rubina, M.; Gevorgyan, V. Recent Advances in Cyclopropene Chemistry (Review). Synthesis 2006, 1221-1245.

Rubin, M.; Rubina, M.; Gevorgyan, V. Transition Metal Chemistry of Cyclopropenes and Cyclopropanes (Review). Chem. Rev. 2007, 107, 3117-3179.