Department Web-Page

Dr. Igor Alabugin
Faculty

Dr. Igor Alabugin

Professor

Ph.D. (1995) Moscow State University

Contact Information
Email:
alabugin@chem.fsu.edu
Office:
5008 CSL 850.644.5795
Lab:
5803 CSL
Programs of Research
 Materials
 Organic
Research Website
Research Specialities
Chemical Biology, Chemistry of Materials, Computational Chemistry and Biochemistry, Photochemistry, Spectroscopy and Dynamics, Supramolecular Chemistry, Synthesis and Catalysis
4 Graduate; 3 Postdoc; 1 Visiting

Research Interest

In short, we study chemical structure and reactivity trying to understand what organic molecules are and what they are capable of. Most of our research is hypothesis-driven and aims to discover new transformations of organic molecules. Reactions previously discovered in our lab have been applied for efficient light-activated cleavage of double-stranded DNA in cancer cells, sequence selective modification of single-stranded oligonucleotides, preparation of complex polycyclic structures related to carbon nanotubes and design of hybrid organic-inorganic materials.

Although the art of making organic molecules plays important role in our projects, the real fun starts once the molecules are made and one's ability to design a system which performs better than Nature is subjected to a critical test! These tests integrate learning and discovery in order to provide students with training for their future careers in organic, physical, analytical and biochemistry both in industry and in academia.

Faculty Interview


Publications

Mechanistic Insights into the Rh(I)-Catalyzed Propargyl Claisen/Prototropic Rearrangement Cascade: Stereoelectronic Role of Trans-Effect on the Pericyclic Process and a Shift from Homogeneous to Heterogeneous Catalysis During a One-Pot Reaction. Vidhani, D. V.; Krafft, M. E.; Alabugin, I. V. J. Org. Chem., in print. http://pubs.acs.org/doi/full/10.1021/jo402505f.
Click chemistry on diterpenes: anti-inflammatory activity of the acetylenic derivatives of levopimaric acid and products of their transformations” Vasilevsky, S. F.; Baranov, D. S.; Govdi, A. I.; Sorokina, I. V.; Tolstikova, T. G.; Tolstikov, G. A. Alabugin, I. V. Submitted.
Exo-Dig Radical Cascades of Skipped Enediynes: Building a Naphthalene Moiety within a Polycyclic Framework. Pati, K.; Hughes, A. M.; Phan, H.; Alabugin, I. V., Chem. Eur. J. 2013, in print. http://onlinelibrary.wiley.com/doi/10.1002/chem.201304092/abstract.
Drawing from a pool of radicals for the design of selective enyne cyclizations. Mondal, S.; Mohamed, R. K.; Manoharan, M.; Phan, H.; Alabugin, I. V. Org. Lett., 2013, 15, 5650–5653. http://pubs.acs.org/doi/abs/10.1021/ol4028072.
Finding the right path: Baldwin “Rules for Ring Closure” and stereoelectronic control of cyclizations. (Invited “Viewpoint”). Alabugin, I. V.; Gilmore, K. Chem. Commun., 2013, 49, 11246 – 11250. http://pubs.rsc.org/en/content/articlehtml/2013/cc/c3cc43872d.
Mohamed, R. K.; Peterson, P. W.; Alabugin, I. V. Concerted Reactions that Produce Diradicals and Zwitterions: Electronic, Steric, Conformational and Kinetic Control of Cycloaromatization Processes. Chem. Rev., 2013, 7089–7129. (invited article, special issue on Reactive Intermediates) http://dx.doi.org/ 10.1021/cr4000682.
Stereocontrolled synthesis of (E, Z)-dienals via tandem Rh(I)-catalyzed rearrangement of propargyl vinyl ethers. Vidhani, D. V.; Krafft, M. E.; Alabugin, I. V. Org. Lett., 2013, 15, 4462-4465. http://dx.doi.org/10.1021/ol4019985.
"Two functional groups in one package": designing cascade transformations of alkynes. (Invited "Synopsis") Alabugin, I. V.; Gold, B. J. Org. Chem., 2013, 78, 7777-7784. http://pubs.acs.org/doi/abs/10.1021/jo401091w.
Peterson, P. W.; Shevchenko, N.; Alabugin, I. V. Stereoelectronic Umpolung”: Converting a p-Donor into a s-Acceptor via Electron Injection and a Conformational Change. Org. Lett. 2013, 15, 2238. http://pubs.acs.org/articlesonrequest/AOR-3EcXR7Src3nze8eT72kg.
Zhan, N.; Palui, G.; Grise, H.; Tang, H.; Alabugin, I.; Mattoussi, H. Combining ligand design with photo-ligation to provide compact, colloidally stable and easy to conjugate quantum dots. ACS Applied Materials & Interfaces (invited). 2013, 5, 2861-2869. http://pubs.acs.org/doi/abs/10.1021/am302788q.
Peterson, P. W.; Mohamed, R. K.; Alabugin, I. V. How to Lose a Bond in Two Ways: The Diradical/Zwitterion Dichotomy in Cycloaromatization Reactions. Invited “Microreview” Eur. J. Org. Chem., 2013, 2013, 2505-2527. http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201656/abstract.
Shatruk, M., Alabugin, I. V. Reinvestigation of "Single-Crystal X-ray Structure of 1,3-dimethylcyclobutadiene.” Chemistry – Eur. Journal, 2013, 19, 4942–4945. http://onlinelibrary.wiley.com/doi/10.1002/chem.201103017/abstract.
Gilmore, K.; Gold, B.; Clark, R.; Alabugin, I. V. Convenient, Ambient Temperature Generation of Sulfonyl Radicals for Addition to Alkynes. Aust. J. Chem., 2013, 66, 336–340. Invited article for a special issue. http://www.publish.csiro.au/?act=view_file&file_id=CH12499.pdf.
Gold, B.; Dudley, G. B.; Alabugin, I. V. Moderating strain without sacrificing reactivity: Design of fast and tunable non-catalyzed alkyne-azide cycloadditions via stereoelectronically controlled transition state stabilization. J. Amer. Chem. Soc., 2013, 135, 1558-1569. http://pubs.acs.org/doi/abs/10.1021/ja3114196.
Vidhani, D. V.; Cran, J. W.; Krafft M. E.; Alabugin, I. V. Gold (I)-Catalyzed Propargyl Claisen Rearrangement: Catalytic Pathways from Higher Energy Au(I)-Substrate Complexes and Reactant Deactivation via Unproductive Complexation. Org. Biomol. Chem., 2013, 11, 1624 - 1630. http://pubs.rsc.org/en/content/articlelanding/2012/OB/C2OB27231H. (Journal Cover).
Vidhani, D. V.; Cran, J. W.; Krafft M. E.; Manoharan, M.; Alabugin, I. V. Gold(I)-Catalyzed Claisen Rearrangement of Allenyl Vinyl Ethers: Missing Transition States Revealed through Evolution of Aromaticity, Au(I) as an Oxophilic Lewis Acid, and Lower Energy Barriers from a High Energy Complex. J. Org. Chem. 2013, 78, 2059–2073 (Special issue dedicated to H. E. Zimmerman). http://pubs.acs.org/doi/abs/10.1021/jo302152j.
Baranov, D.; Gold, B.; Vasilevsky, S.; Alabugin, I. V. Divergent Cyclizations of 1-R-Ethynyl-9,10-anthraquinones: Use of Thiourea as a "S2-" Equivalent in an "Anchor-Relay" Addition Mediated by Formal C-H Activation. J. Org. Chem. 2013, 78, 2074-2082 (Special issue dedicated to H. E. Zimmerman). http://pubs.acs.org/doi/pdf/10.1021/jo302146r.