Michael Rubin


Michael Rubin
  • Associate Professor

Contact Info

Phone:
3152B GL (ISB)
Lawrence
1567 Irving Hill Rd
Lawrence, KS 66045

Education

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

Specialization

  • Synthetic Methodology
  • Transition Metal Catalysis
  • Physical Organic Chemistry

Research

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.


Rubin Research


Rubin Research

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.


Rubin Research

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.


Rubin Research


Rubin Research

Selected Publications

Aksenov, A.V.; Aksenov, N.A.; Aleksandrova, E.V.; Aksenov, D.A.; Grishin, I.Y.; Sorokina, E.A.; Wenger, A.; Rubin, M. Direct Conversion of 3-(2-Nitroethyl)-1H-Indoles into 2-(1H-Indol-2-yl)Acetonitriles. Molecules 202126, 6132. https://doi.org/10.3390/molecules26206132.

Dmitrii A. Aksenov, Alexander V. Aksenov, Lidiya A. Prityko, Nicolai A. Aksenov, Liliya V. Frolova, Michael Rubin. Methylation of 2-aryl-2-(3-indolyl)acetohydroxamic acids and evaluation of anti-cancer activity of the products.  Molbank2022, M1307. https://doi.org/10.3390/M1307

Alexander V. Aksenov, Elena V. Aleksandrova, Dmitrii A. Aksenov, Anna A. Aksenova, Nicolai A. Aksenov, Mezvah A. Nobi, Michael Rubin. Synthetic studies towards 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indole core.  Unusual Fragmentation with 1,2-Aryl ShiftJ. Org. Chem.2022, 87, 1434−1444. DOI: 10.1021/acs.joc.1c02753.

Alexander V. Aksenov, Nikita K. Kirilov, Nicolai A. Aksenov, Nikolai A. Arutiunov, Dmitrii A. Aksenov, and Michael Rubin.  Electrophilically activated nitroalkanes in synthesis of functionally substituted 1,3,4-oxadiazoles from aminoacid derivativesChem. Heterocycl. Comp.2022, 58(1), 32-36.

Michael Rubin, Nicolai A. Aksenov, Anton A. Skomorokhov, Dmitrii A. Aksenov, Igor A. Kurenkov,  Elena A. Sorokina, Nikita K. Kirilov, Mezvah A. Nobi, Alexander V. Aksenov.  Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?RSC Advances, 2021, 11(57), 35937 – 35945.  DOI: 10.1039/d1ra06503c

Alexander V. Aksenov, Nicolai A. Aksenov, Elena V. Aleksandrova, Dmitrii A. Aksenov, Igor Yu. Grishin, Elena A. Sorokina, Allison Wenger, Michael Rubin.  Direct conversion of 3-(2-nitroethyl)-1H-indoles into 2-(1H-indol-2-yl)acetonitrilesMolecules2021, 26(20), 6132;  DOI: 10.3390/molecules26206132 Link: https://doi.org/10.3390/molecules26206132

Dmitrii A. Aksenov, Nikolai A. Arutyunov, Amina Z. Gasanova, Nicolai A. Aksenov, Alexander V. Aksenov, Carolyn Lower, and Michael Rubin.  Synthetic studies towards benzofuro[2,3-b]quinoline and 6H-indolo[2,3-b]quinoline cores: Total synthesis of Norneocryptolepine and Neocryptolepine. Tetrahedron Letters2021, 82, 153395.  DOI: 10.1016/j.tetlet.2021.153395

Alexander V. Aksenov, Nikita K. Kirilov, Nicolai A. Aksenov, Dmitrii A. Aksenov, Elena A. Sorokina, Carolyn Lower, and Michael Rubin.  Electrophilically activated nitroalkanes in double annulation of [1,2,4]triazolo­[4,3-a]quinolines and 1,3,4-oxadiazole ringsMolecules2021, 26(18), 5692.  DOI: 10.3390/molecules26185692

Alexander V. Aksenov, Igor Yu. Grishin, Nicolai A. Aksenov, Vladimir V. Malyuga, Dmitrii A. Aksenov, Mezvah A. Nobi, and Michael Rubin.  Electrophilically activated nitroalkenes in synthesis of 3,4-dihydroquinozalinesMolecules, 2021, 26(14), 4274 (15 pp).  DOI: 10.3390/molecules26144274  https://www.mdpi.com/1420-3049/26/14/4274

Alexander V. Aksenov, Nikolai A. Arutiunov, Nikita K. Kirilov, Dmitrii A. Aksenov, Igor Yu. Grishin, Nicolai A. Aksenov, Huifen Wang, Liqin Du, Tania Betancourt, Stephen C. Pelly, Alexander Kornienko, and Michael Rubin.  [3+2]-Annulation of pyridinium ylides with 1-chloro-2-nitrostyrenes unveils a tubulin polymerization inhibitorOrg. Biomol. Chem., 2021, 19(33), 7234–7245.  DOI: 10.1039/d1ob01141c

Pavel M. Yamanushkin, Marina Rubina, Michael Rubin. Amide-Directed Reactions of Small Carbocycles. Current Organic Chemistry, 2021, 25(14), 1686-1703. DOI: 10.2174/1385272825666210706124215