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 research projects are shown below in
Schemes 1-5.
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 (click here for full
list):
Preparation and X-ray crystal study of benziodoxaborole
derivatives: new hypervalent iodine heterocycles. Nemykin, V.N.;
Maskaev, A.V.; Geraskina, M.R.; Yusubov, M.S.; Zhdankin, V.V. Inorg. Chem. 2011, 50, 11263-11272.
SiO2-supported RuCl3/3-(dichloroiodo)benzoic acid: green
catalytic
system for the oxidation of alcohols and sulfides in water. Zeng,
X.-M.; Chen, J.-M.; Yoshimura, A.; Middleton, K.; Zhdankin, V.V. RSC Advances 2011, 1, 973-977.
Recyclable silica-supported iodoarene-RuCl3 bifunctional catalysts
for oxidation of alcohols and alkylarenes. Zeng, X.-M.; Chen, J.-M.;
Middleton, K.; Zhdankin, V.V. Tetrahedron
Lett. 2011, 52, 5652–5655.
o-Alkoxyphenyliminoiodanes:
Highly Efficient Reagents for Catalytic Aziridination of Alkenes and
Metal-Free Aminations of Organic Substrates. Yoshimura, A.; Nemykin,
V.N.; Zhdankin, V.V. Chem. Eur. J.
2011, 17, 10538-10541.
Iodonium salts in organic synthesis. Yusubov, M.S.; Maskaev, A.V.;
Zhdankin, V.V. ARKIVOC 2011, (i), 370-409.
Hypervalent Iodine Reagents and Green Chemistry. Yusubov, M.S.;
Zhdankin, V.V. Curr. Org. Synth.
2011, 8, E-Pub, doi:
10.2174/1570211700120991794.
Preparation and Reactivity of Polystyrene-supported Iodosylbenzene:
Convenient Recyclable Oxidizing Reagent and Catalyst. Chen, J.-M.;
Zeng, X.-M.; Middleton, K.; Yusubov, M.S.; Zhdankin, V.V. Synlett 2011, 1613-1617.
Preparation, X-ray Structure and Reactivity of
2-Iodylpyridines:
Recyclable Hypervalent Iodine(V) Reagents. Yoshimura, A.; Banek, C.T.;
Yusubov, M.S.; Nemykin, V.N.; Zhdankin, V.V. J. Org. Chem. 2011, 76, 3812-3819.
Organoiodine(V) Reagents in Organic Synthesis. Zhdankin,
V.V. J. Org. Chem. 2011, 76, 1185-1197. (Perspective article
with associated cover art)
Facile preparation and reactivity of polystyrene-supported
(dichloroiodo)benzene: a convenient recyclable reagent for
chlorinations and oxidations. Chen, J.-M.; Zeng, X.-M.; Middleton,
K.;
Zhdankin, V.V. Tetrahedron Lett.
2011, 52, 1952-1955.
Hofmann Rearrangement of Carboxamides Mediated by
Hypervalent Iodine
Species Generated in situ from Iodobenzene and Oxone: Reaction Scope
and Limitations. Zagulyaeva, A.A.; Banek, C.T.; Yusubov, M.S.;
Zhdankin, V.V. Org. Lett. 2010, 12, 4644-4647.
Preparation and Reactivity of Polystyrene-Supported Iodosylbenzene
Sulfate, an Efficient Recyclable Oxidizing System. Chen, J.-M.; Zeng,
X.-M.; Zhdankin, V.V. Synlett
2010, 2771-2774.
m-Iodosylbenzoic acid as a
convenient recyclable hypervalent iodine oxidant for the synthesis of
α-iodoketones by oxidative iodination of ketones. Yusubov, M.S.;
Yusubova, R.Y.; Funk, T.V.; Chi, K.-W.; Kirschning, A.; Zhdankin, V.V. Synthesis 2010, 3681-3685.
Metalloporphyrin/Iodine(III)-Cocatalyzed Oxygenation of Aromatic
Hydrocarbons. Yoshimura, A.; Neu, H.M.; Nemykin, V.N.; Zhdankin, V.V. Adv. Synth. Cat. 2010, 352, 1455-1460.
Transition Metal-mediated Oxidations Utilizing Monomeric Iodosyl-
and Iodylarene Species. Yusubov, M.S.; Nemykin, V.N.; Zhdankin, V.V. Tetrahedron 2010, 66, 5745-5752.
Development of New Recyclable Reagents and Catalytic Systems Based on
Hypervalent Iodine Compounds. Yusubov, M.S.; Zhdankin, V.V. Mendeleev Commun. 2010, 20, 185-191.
A General and Convenient Preparation of
[Bis(trifluoroacetoxy)iodo]perfluoroalkanes and
[Bis(trifluoroacetoxy)iodo]arenes by Oxidation of Organic Iodides using
Oxone and Trifluoroacetic Acid. Zagulyaeva, A.A.; Yusubov, M.S.;
Zhdankin, V.V. J. Org. Chem.
2010, 75, 2119-2122.
Binuclear Iron(III) Phthalocyanine(μ-Oxodimer)-Catalyzed
Oxygenation of Aromatic Hydrocarbons with Iodosylbenzene Sulfate and
Iodosylbenzene as the Oxidants. Neu, H.M.; Yusubov, M.S.; Zhdankin,
V.V.; Nemykin, V.N. Adv. Synth. Cat.
2009, 351, 3168-3174.
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, 5399-5358.
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 Reactivity of Polymer-Supported 2-Iodylphenol Ethers,
an Efficient Recyclable Oxidizing System. Karimov, R.R.; Kazhkenov,
Z.M.; Modjewski, M.J.; Peterson, E.M.; Zhdankin, V.V. J. Org. Chem. 2007, 72, 8149-8151.
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
Aryliodonium 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.
Books
Handbook of Heterocyclic Chemistry,
3rd Edition. Katritzky, A.R.; Ramsden, C.A.; Joule, J.A.;
Zhdankin, V.V. Elsevier, Oxford, 2010; ISBN 0080958435.
Hypervalent Iodine Chemistry-Modern
Developments in Organic Synthesis. Top. Curr. Chem. 224. Wirth,
T.; Ochiai, M.; Zhdankin, V. V.; Koser, G. F.; Tohma, H.; Kita, Y.
Springer: Berlin, 2003.
Edited Books
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.
Full
CV
in PDF format
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