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Roman Dembinski

Roman Dembinski

Title: Associate Professor
Organic Chemistry
Office: 225 Science and Engineering Building
Phone: (248) 370-2248
E-mail: dembinsk@oakland.edu
Research Group

Degrees
Ph.D., Polish Academy of Sciences, Lodz

Research Interests

Professor Dembinski and his students are pursuing at present the synthesis of analogs of natural products, particularly coordination complexes of nucleosides and nucleotides. The abundance of various metals with different coordination numbers, geometry and redox potentials makes their combination with natural products a powerful tool for the construction of modified biomolecules. Ongoing efforts also include incorporation of perfluoroalkyl "ponytails" (CH2)n(CF2)mCF3 into the molecules. Variation of the number of "spacers" (CH2 groups between strong electron withdrawing CF2 and the modified part) and the perfluoroalkyl chain lengths can be used to fine-tune electronic properties. It is expected that such modified molecules may exhibit interesting biological properties. Some may serve as “fluorous” tags, reagents or catalysts. The ultimate goal of these studies is to synthesize materials that exhibit antiviral, anticancer, antisense properties, serve as bio-probes, and to develop new synthetic methodologies.

Representative Publications

Yan Li, Kraig A. Wheeler, and Roman Dembinski, Room Temperature Syntheses of Entirely Diverse Substituted beta-Fluorofurans. Org. Biomol. Chem.201210, 2395-2408. Cover Article.

Roman Dembinski, Yan Li, Deepthi Gundapuneni, Alicia Decker, Synthesis of beta -Halofurans. In Halogenated Heterocycles: Synthesis and Use; Iskra, J., Ed.; series Top. Heterocycl. Chem.; Springer: Heidelberg, 2012, vol 27, ch. 3, 65-100.

Yan Li, Kraig A. Wheeler, and Roman Dembinski, Electrophilic Cyclizations of 2-Fluoroalk-3-yn-1-ones: Room Temperature Synthesis of Diversely 2,5-Substituted 3,4 Fluorohalofurans. Eur. J. Org. Chem. 2011, 2767-2771.

Yan Li, Kraig A. Wheeler, and Roman Dembinski, Gold(I)-Catalyzed Cycloisomerization of 2-Fluoroalk-3-yn-1-ones: Synthesis of 2,5-Substituted 3-Fluorofuran, Adv. Synth. Catal. 2010352, 2761-2766.

Adam Sniady, Michael D. Sevilla, Srinivasarao Meneni, Tadeusz Lis, Slawomir Szafert, Deepthi Khanduri, John M. Finke, and Roman Dembinski, Synthesis and ESR studies of 2'-deoxyuridines tethered with alkynyl, rod-like linkagesChem. Eur. J. 200915, 7569-7577. Cover Article, issue 31.

Przemyslaw Wyrebek, Adam Sniady, Nicholas Bewick, Yan Li, Agnieszka Mikus, Kraig A. Wheeler, and Roman Dembinski,Microwave-Assisted Zinc Chloride-Catalyzed Synthesis of Substituted Pyrroles from Homopropargylic Azides,Tetrahedron 200965, 1268-1275.

Adam Sniady, Marco S. Morreale, Kraig A. Wheeler, and Roman Dembinski, Room Temperature Electrophilic 5-Endo-digChlorocyclization of Alk-3-yn-1-ones with the use of Pool Sanitizer: Synthesis of 3-Chlorofurans and 5-Chlorofuropyrimidine NucleosidesEur. J. Org. Chem. 20083449-3452Cover Article. Among top 8 most accessed articles 6/2008.

Adam Sniady, Audrey Durham, Marco S. Morreale, Andrzej Marcinek, Slawomir Szafert, Tadeusz Lis, Krystyna R. Brzezinska, Takanori Iwasaki, Takashi Ohshima, Kazushi Mashima, and Roman Dembinski, Zinc-Catalyzed Cycloisomerizations. Synthesis of Substituted Furans and Furopyrimidine NucleosidesJ. Org. Chem. 200873, 5881-5889.

Craig D. Sergeant, Ingo Ott, Adam Sniady, Srinivasarao Meneni, Ronald Gust, Arnold L. Rheingold, and Roman Dembinski,Metallo-Nucleosides: Synthesis and Biological Evaluation of Hexacarbonyl Dicobalt 5-Alkynyl-2'-DeoxyuridinesOrg. Biomol. Chem. 20086, 73-80. Cover Article, issue 1.

Roman Dembinski, Pablo Espinet, Sergio Lentijo, Marcin W. Markowicz, Jose M. Martín-Alvarez, Arnold L. Rheingold, Daniel J. Schmidt, and Adam Sniady, Fluorophobic effect in metallomesogens. The synthesis and mesomorphism of Ag, Au, Cu, Fe, Pd, and Pt fluorous isocyanide complexesEur. J. Inorg. Chem. 2008, 1565-1572.

Adam Sniady, Audrey Durham, Marco S. Morreale, Kraig A. Wheeler, and Roman Dembinski, Room Temperature Zinc Chloride-Catalyzed Cycloisomerization of Alk-3-yn-1-ones: Synthesis of Substituted FuransOrg. Lett. 20079, 1175-1178.

Srinivasarao Meneni, Ingo Ott, Craig D. Sergeant, Adam Sniady, Ronald Gust, and Roman Dembinski, 5-Alkynyl-2'-Deoxyuridines: Chromatography-Free Synthesis and Cytotoxicity Evaluation Against Human Breast Cancer Cells,Bioorg. Med. Chem. 200715, 3082-3088.

Adam Sniady, Marco S. Morreale, and Roman Dembinski, Electrophilic cyclization with N-Iodosuccinimide: Preparation of 5-(4-bromophenyl)-3-iodo-2-(4-methylphenyl)furanOrg. Synth. 200784, 199-208.

Zoltán Kaleta, Brian T. Makowski, Tibor Soós, and Roman Dembinski, Thionation using Fluorous Lawesson’s ReagentOrg. Lett. 20068, 1625-1628.

Maria Angeles Ubeda and Roman Dembinski, Fluorous Compounds and Their Role in Separation ChemistryJ. Chem. Educ. 200683, 84-92.

Adam Sniady, Kraig A. Wheeler, and Roman Dembinski, 5-Endo-dig Electrophilic Cyclization of 1,4-Disubstituted But-3-yn-1-ones: Regiocontrolled Synthesis of 3-Bromo- and 3-Iodo-2,5-Disubstituted FuransOrg. Lett. 20057, 1769-1772.

Roman Dembinski, Recent Advances in the Mitsunobu Reaction: Modified Reagents and the Quest for Chromatography-Free SeparationEur. J. Org. Chem. 2004, 2763-2772. Most accessed article in 2004.

Roman Dembinski, Approaches to Fluorous Mitsunobu Reaction, In Handbook of Fluorous Chemistry, Wiley-VCH: Weinheim, 2004, Chapter 10.3, pp 190-202.

Marcin W. Markowicz and Roman Dembinski, Fluorous Coupling Reagents: Application of 2-Chloro-4,6-bis[(heptadecafluoronyl)oxy]-1,3,5-triazine in Peptide Synthesis, Synthesis 2004, 80-86.

Meneni Srinivasa Rao, Noor Esho, Craig Sergeant, and Roman Dembinski, 5-Endo-dig Electrophilic Cyclization of alpha -Alkynyl Carbonyl Compounds: Synthesis of Novel Bicyclic 5-Iodo- and 5-Bromofurano Pyrimidine NucleosidesJ. Org. Chem. 200368, 6788-6790.

Marcin W. Markowicz and Roman Dembinski, Fluorous, Chromatography-Free Mitsunobu ReactionOrg. Lett. 20024, 3785-3788.

Noor Esho, Brian Davies, Janet Lee, and Roman Dembinski, Synthesis of dicobalt hexacarbonyl 5-p-tolylethynyl-2'-deoxyuridine, Chem. Commun. 2002, 332-333.

Roman Dembinski, Tamas Bartik, Berit Bartik, Monika Jaeger, and J. A. Gladysz, Towards Metal-Capped One-Dimensional Carbon Allotropes: Wirelike C6-C20 Polyalkynediyl Chains that Span Two Redox-Active (h5-C5Me5)Re(NO)(PPh3) Endgroups, J. Am. Chem. Soc. 2000122, 810.

Full List of Publications 
Recent X-ray


Publicity

3-Fluorofurans (Synfacts 2011) 
Fun with Fluorinated Furans 
Synform (March 2009) 
Chlorofurans (Synfact of the Month) 
Zinc Chloride Catalysis (Synfacts 2008) 
Most Accessed Articles (2007) 
Zinc Chloride Catalyzed Synthesis of Furans (www.organic-chemistry.org) 
Write Stuff (C&EN, August 13, 2007) 
Zinc Chloride Catalysis (Synfacts 2007) 
Fluorous Lawesson's Reagent (www.organic-chemistry.org) 
Featured Molecules in J.Chem. Educ. 
Synthesis of 3-Halofurans (www.organic-chemistry.org) 
Recent Advances in the Mitsunobu Reaction (the most often downloaded Eur. J. Org. Chem. article) 
Fluorous Chlorotriazine (commercialized)
Fluorous Acyl Donor for Mitsunobu Reaction (the covette of the Chem. Eur. J. article) 
Science Editor's Choice


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