Department of Chemistry and Biochemistry

Viktor V. Zhdankin
Research Description

    Our research program in general is aimed at the development of new synthetic methodologies based on the organic chemistry of hypervalent main-group elements. Hypervalent compounds are generally defined as “ions or molecules of the elements of Groups 15-18 bearing more electrons than the octet within a valence shell”. In current synthetic literature, this terminology is commonly applied toward the synthetically useful organic reagents, derivatives of main-group elements in high oxidation states, such as polyvalent iodine, tellurium, selenium, antimony, and bismuth. It has been recognized that there are many similarities between hypervalent main group compounds and organic transition metal complexes. The reactions of hypervalent molecules are commonly discussed in terms of oxidative addition, reductive elimination, ligand exchange, and ligand coupling, which are typical of the transition metal chemistry. Exploration and practical utilization of these similarities may lead to the development of new useful methodologies for modern organic synthesis. Compared to other hypervalent main-group elements, the chemistry of hypervalent iodine(III) and iodine(V) compounds has attracted a special research interest due to the very useful oxidizing properties of these compounds, combined with their benign environmental character .
    Specific objectives of our current research program include: (i) the development of new oxidizing reagents based on organic compounds of iodine(III) and iodine(V), (ii) the development of polymer-supported and recyclable hypervalent iodine reagents, and (iii) the catalytic applications of hypervalent organoiodine compounds. Several examples of our recent research projects are shown below in Schemes 1-5.


Scheme 1


Scheme 2


Scheme 3


Scheme 4


  Scheme 5

    Other areas of our research interests include the chemistry of organoxenon(II) compounds, organoboronic acids, synthetic organofluorine chemistry, and the chemistry of acetylenes.



 



SELECTED RECENT PUBLICATIONS  

Preparation, X-ray Structure, and Oxidative Reactivity of N-(2-Iodylphenyl)tosylamides and 2-Iodylphenyl Tosylate: Iodylarenes Stabilized by Ortho-Substitution with a Sulfonyl Group. Mailyan, A.K; Geraskin, I.M.; Nemykin, V.N.; Zhdankin, V.V. J. Org. Chem.  2009, 74, 8444-8447.

Iodine(V)/Ruthenium(III)-Cocatalyzed Oxidations: A Highly Efficient Tandem Catalytic System for the Oxidation of Alcohols and Hydrocarbons with Oxone. Yusubov, M.S.; Zagulyaeva, A.A.; Zhdankin, V.V. Chem. Eur. J.  2009, 15, 11091-11094.

Oligomeric iodosylbenzene sulfate, (PhIO)3•SO3: Convenient hypervalent iodine reagent for oxidation of organic sulfides and alkenes. Yusubov, M.S.; Yusubova, M.S.; Funk, T.V.; Chi, K.-W.; Zhdankin, V.V. Synthesis 2009, 2505-2508.

Self-assembly of hydroxy(phenyl)iodonium ions in acidic aqueous solution: preparation, and X-ray crystal structures of oligomeric phenyliodine(III) sulfates. Nemykin, V.N.; Koposov, A.Y.; Netzel, B.C.; Yusubov, M.S.; Zhdankin, V.V. Inorg. Chem. 2009, 48, 4908-4917.

Comparative Reactivity of Hypervalent Iodine Oxidants in Metalloporphyrin-Catalyzed Oxygenation of Hydrocarbons: Iodosylbenzene Sulfate and 2-Iodylbenzoic Acid Ester as Safe and Convenient Alternatives to Iodosylbenzene. Geraskin, I.M.; Pavlova, O.; Neu, H.M.; Yusubov, M.S.; Nemykin, V.N.; Zhdankin, V.V. Adv. Synth. Cat. 2009, 351, 733-737.

Hypervalent Iodine(III) Reagents in Organic Synthesis. Zhdankin, V.V. ARKIVOC 2009, (i), 1-62.

Chemistry of Polyvalent Iodine. Zhdankin, V.V.; Stang, P.J. Chem. Rev. 2008, 108, 5299-5358.

Preparation and X-ray crystal structure of 2-iodyl-N,N-dialkylaniline oxides: first entry into the heterocyclic system of benziodoxazole. Zhdankin, V.V.; Nemykin, V.N.; Karimov, R.R.; Kazhkenov, Z.M. Chem. Commun. 2008, 6131-6133.

Organic iodine(V) compounds as terminal oxidants in iron(III) phthalocyanine catalyzed oxidation of alcohols. Geraskin, I.M.; Luedtke, M.W.; Neu, H.M.; Nemykin, V.N.; Zhdankin, V.V. Tetrahedron Lett. 2008, 49, 7410-7412.

Synthesis of Tricyclic Phosphono Pyrrolidines via IMDAF: Experimental and Theoretical Investigation of the Observed Stereoselectivity. Claeys, D.D.; Moonen, K.; Roman, B.I.; Nemykin, V.N.; Zhdankin, V.V.; Waroquier, M.; Speybroeck, V.V.; Stevens, C.V. J. Org. Chem. 2008, 73, 7921-7927.

Comprehensive Heterocyclic Chemistry III, Volume 5 (10 chapters): “Triazoles, Oxadiazoles, Thiadiazoles and their Fused Carbocyclic Derivatives,” V.V. Zhdankin, Ed.; Elsevier, Oxford, 2008.

Comprehensive Heterocyclic Chemistry III, Volume 6 (18 chapters): “Other Five-Membered Rings with Three or More Heteroatoms and their Fused Carbocyclic Derivatives,” V.V. Zhdankin, Ed.; Elsevier, Oxford, 2008.

Heterocycles with Three or Four Heteroatoms Including At Least One Phosphorus. Zhdankin, V.V. In Comprehensive Heterocyclic Chemistry III. Katritzky, A.R.; Ramsden, C.A.; Scriven, E.F.V.; Taylor, R.J.K., Eds.; Elsevier, Oxford, 2008, Vol. 6, Chapter 13, pp 583-602.

Preparation and X-ray Structures of 3-[Bis(trifluoroacetoxy)iodo]benzoic acid and 3-[Hydroxy(tosyloxy)iodo]benzoic acid, New Recyclable Hypervalent Iodine Reagents. Yusubov, M.S.; Funk, T.V.; Chi, K.-W.; Cha, E.-H.; Ghyung, H.K.; Kirschning, A.; Zhdankin, V.V. J. Org. Chem. 2008, 73, 295-297.

Preparation and Structure of Oligomeric Iodosylbenzene Sulfate (PhIO)3•SO3: Stable and Water-soluble Analog of Iodosylbenzene. Koposov, A.Y.; Netzel, B.C.; Yusubov, M.S.; Nemykin, V.N.; Nazarenko, A.Y.; Zhdankin, V.V. Eur. J. Org. Chem. 2007, 4475-4478.

Hypervalent Iodoarenes and Arene Iodonium Salts. Zhdankin, V.V. Science of Synthesis, 2007, 31, Ch. 31.4.1  161-234.

N-(2-Iodylphenyl)acylamides - New Pentavalent Iodine Oxidizing Reagents. Ladziata, U.; Zhdankin, V.V. Synlett 2007, 527-537.

m-Iodosylbenzoic Acid as a Convenient Recyclable Reagent for Highly Efficient RuCl3-Catalyzed Oxidation of Alcohols to Carbonyl Compounds. Yusubov, M.S.; Gilmkhanova, M.P.; Zhdankin, V.V.; Kirschning, A. Synlett 2007, 563-566.

trans Influences on Hypervalent Bonding of Aryl λ3-Iodanes: Their Stabilities and Isodesmic Reactions of Benziodoxolones and Benziodazolones. Ochiai, M.; Sueda, T.; Miyamoto, K.; Kiprof, P.; Zhdankin, V.V. Angew. Chem. Int. Ed. 2006, 45, 8203-8206.

Hypervalent Iodine(V) Reagents in Organic Synthesis. Ladziata, U.; Zhdankin, V.V. ARKIVOC 2006, (ix), 26-58.

Facile Preparation and Reactivity of Polymer-Supported N-(2-Iodyl-phenyl)-acylamide, an Efficient Oxidizing System. Ladziata, U.; Willging, J.; Zhdankin, V.V. Org. Lett. 2006, 7, 167-170.

Highly Efficient RuCl3-Catalyzed Disproportionation of (Diacetoxyiodo)benzene to Iodylbenzene and Iodobenzene; Leading to the Efficient Oxidation of Alcohols to Carbonyl Compounds. Yusubov, M.S.; Chi, K.-W.; Park, J.Y.; Karimov, R.; Zhdankin, V.V. Tetrahedron Lett. 2006, 47, 6305-6308.

Synthesis and Oxidative Reactivity of New Chiral Hypervalent Iodine(V) Reagents Based on (S)-Proline. Ladziata, U.; Carlson, J.; Zhdankin, V.V. Tetrahedron Lett. 2006, 47, 6301-6304.

Preparation and Reductive Decomposition of 2-Iodoxybenzenesulfonic Acid; X-Ray Crystal Structure of 1H-1-Hydroxy-1,2,3-benziodoxathiole 3,3-dioxide. Koposov, A.Y.; Litvinov, D.N.; Zhdankin, V.V.; Ferguson, M.J.; McDonald, R.; Tykwinski, R.R. Eur. J. Org. Chem. 2006, 4791-4795.

2-Iodylphenol Ethers: Preparation, X-Ray Crystal Structure, and Reactivity of New Hypervalent Iodine(V) Oxidizing Reagents. Koposov, A.Y.; Karimov, R.R.; Geraskin, I.; Nemykin, V.N.; Zhdankin, V.V. J. Org. Chem. 2006, 71, 8452-8458.

RuCl3-catalyzed Oxidation of Iodoarenes with Peracetic Acid: New Facile Preparation of Iodylarenes. Koposov, A.Y.; Karimov, R.R.; Pronin, A.A.; Skrupskaya, T.; Yusubov, M.S.; Zhdankin, V.V. J. Org. Chem. 2006, 71, 9912-9914.

Selective Oxidation of Sulfides to Sulfoxides Using IBX-Esters. Koposov, A.Y.; Zhdankin, V.V. Synthesis 2005, 22-25.

Derivatives of 2-Iodoxybenzenesulfonic Acid: New Pseudocyclic Hypervalent Iodine Reagents. Zhdankin, V.V.; Goncharenko, R.N.; Litvinov, D.N.; Koposov, A.Y. ARKIVOC 2005, (4), 8-18.

Benziodoxole-Based Hypervalent Iodine Reagents in Organic Synthesis. Zhdankin, V.V. Curr. Org. Synth. 2005, 2, 121-145.

Esters of 2-Iodoxybenzoic Acid (IBX-Esters): Hypervalent Iodine Oxidizing Reagents with a Pseudobenziodoxole Structure. Zhdankin, V.V.; Koposov, A.Y.; Litvinov, D.N.; Ferguson, M.J.; McDonald, R.; Luu, T.; Tykwinski, R.R. J. Org. Chem. 2005, 70, 6484-6491.

Intra- and Intermolecular Interactions in the Solid State Structure of 2-Iodylbenzenesulfonamides: a Heptacoordinated Organic Iodine(V) Compound. Koposov, A.Y.; Nemykin, V.N.; Zhdankin, V.V. New J. Chem. 2005, 29, 998-1000.

Synthesis, Structure and Chemoselective Reactivity of N-(2-Iodylphenyl)-acylamides, Novel Hypervalent Iodine Reagents Bearing Pseudo Six-membered Ring Scaffold. Ladziata, U.; Koposov, A.Y.; Lo, K.Y.; Willging, J.; Nemykin, V.N.; Zhdankin, V.V. Angew. Chem. Int. Ed. 2005, 44, 7127-7131.

Alkynyl Halides and Chalcogenides. Zhdankin, V.V. In Comprehensive Organic Functional Group Transformations II. Katritzky, A.R.; Taylor, R.J.K., Eds.; Elsevier, Oxford, 2004, Vol. 2, Chapter 21, 1073-1114.

Preparation and Structure of 2-Iodoxybenzoate Esters: Soluble and Stable Periodinane Oxidizing Reagents. Zhdankin, V.V.; Litvinov, D.N.; Koposov, A.Y.; Luu, T.; Ferguson, M.J.; McDonald, R.; Tykwinski, R.R. J. Chem. Soc., Chem. Commun. 2004, 106-107.

2-Iodoxybenzenesulfamides: New Pseudobenziodoxole-Based Hypervalent Iodine Reagents. Koposov, A.Y.; Litvinov, D.N.; Zhdankin, V.V. Tetrahedron Lett. 2004, 45, 2719-2721.

4,4'-Bis(dichloroiodo)biphenyl and 3-(Dichloroiodo)benzoic Acid: New Recyclable Hypervalent Iodine Reagents for Vicinal Halomethoxylation of Unsaturated Compounds. Yusubov, M.S.; Drygunova, L.A.; Zhdankin, V.V. Synthesis 2004, 2289-2292.

Amino acid-derived iodobenzene dicarboxylates: Reagents for oxidative conversion of alkenes to amino acid esters. Koposov, A.Y.; Boyarskikh, V.V.; Zhdankin, V.V.  Org. Lett. 2004, 6, 3613-3615.

C–C Bond Forming Reactions. Zhdankin, V.V. In Topics in Current Chemistry, Vol. 224, Wirth, T., Ed.; Springer-Verlag, Berlin Heidelberg, 2003, Chapter 4, pp. 99-136.
Preparation and Chemistry of Phosphorane-Derived Iodanes. Zhdankin, V.V.; Maydanovych, O.; Herschbach, J.; Bruno, J.; Matveeva, E.D.; Zefirov, N.S. J. Org. Chem. 2003, 68, 1018-1023. 

IBX Amides: New Family of Hypervalent Iodine Reagents. Zhdankin, V.V.; Koposov, A.Y.; Netzel, B.C.; Yashin, N.V.; Rempel, B.P.; Ferguson, M.J.; Tykwinski, R.R. Angew. Chem. Int. Ed. 2003, 42, 2194-2196. (Placed on Angew. Chem. Hot Articles Website).

Synthesis and Structure of Amino Acid-Derived Benziodazoles: New Hypervalent Iodine Heterocycles. Zhdankin, V.V.; Koposov, A.Y.; Su, L.; Boyarskikh, V.V.; Netzel, B.C.; Young, V.G. Org. Lett. 2003, 5, 1583-1586. (Placed on ACS Hot Articles Website).

Recent Developments in the Chemistry of Polyvalent Iodine Compounds. Zhdankin, V.V.; Stang, P.J. Chem. Rev. 2002, 102, 2523-2584.

Complexes of Hypervalent Iodine Compounds with Nitrogen Ligands. Zhdankin, V.V.; Koposov, A.Y.; Yashin, N.V. Tetrahedron Lett. 2002, 42, 5735-5737.

Preparation, Structure, and Unexpected Chemistry of Phosphoranyl Derived Benziodoxoles. Zhdankin, V.V.; Maydanovych, O.; Herschbach, J.; Tykwinski, R.R.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 11614-11615.

Functionalization of Buckminsterfullerene by Hypervalent Iodine Reagents. Zhdankin, V.V.; Hanson, K.J.; Koposov, A.E.; Blomquist, E.; Tykwinski, R.R. Mendeleev Commun. 2001, 51-52.

Secondary Bonding-Directed Self-Assembly of Amino Acid Derived Benziodazoles: Synthesis and Structure of Novel Hypervalent Iodine Macrocycles. Zhdankin, V.V.; Koposov, A.E.; Smart, J.T.; Tykwinski, R.R.; McDonald, R.; Morales-Izquierdo, A. J. Am. Chem. Soc. 2001, 123, 4095-4096.

 


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Updated June, 2008