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Pure Appl. Chem., 1999, Vol. 71, No. 3, pp. 431-436

http://dx.doi.org/10.1351/pac199971030431

Transferring iodine: more than a simple functional group exchange in organic synthesis

J. Barluenga

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  • Bedrač Leon, Iskra Jernej: Iodine(I) Reagents in Hydrochloric Acid-Catalyzed Oxidative Iodination of Aromatic Compounds by Hydrogen Peroxide and Iodine. Adv. Synth. Catal. 2013, 355, 1243. <http://dx.doi.org/10.1002/adsc.201300127>
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  • Fraser-Reid Bert, Lopez J. Cristobal, Bernal-Albert Paloma, Gomez Ana M., Uriel Clara, Ventura Juan: Glycosyl fluorides from n-pentenyl-related glycosyl donors — Application to glycosylation strategies. Can. J. Chem. 2013, 91, 51. <http://dx.doi.org/10.1139/cjc-2012-0285>
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  • Chávez Patricia, Kirsch Jonathan, Hövelmann Claas H., Streuff Jan, Martínez-Belmonte Marta, Escudero-Adán Eduardo C., Martin Eddy, Muñiz Kilian: Metal-free diamination of alkenes employing bromide catalysis. Chem. Sci. 2012, 3, 2375. <http://dx.doi.org/10.1039/c2sc20242e>
  • Hashmi A. Stephen K., Schuster Andreas M., Schmuck Martin, Rominger Frank: Gold-Catalyzed Cyclization of Nonterminal Propargylic Amides to Substituted Alkylideneoxazolines and -oxazines. Eur J Org Chem 2011, 2011, 4595. <http://dx.doi.org/10.1002/ejoc.201100342>
  • Marri Mahender Reddy, Macharla Arun Kumar, Peraka Swamy, Nama Narender: Oxidative iodination of carbonyl compounds using ammonium iodide and oxone®. Tetrahedron Letters 2011, 52, 6554. <http://dx.doi.org/10.1016/j.tetlet.2011.09.106>
  • Weyrauch Jan P., Hashmi A. Stephen K., Schuster Andreas, Hengst Tobias, Schetter Stefanie, Littmann Anna, Rudolph Matthias, Hamzic Melissa, Visus Jorge, Rominger Frank, Frey Wolfgang, Bats Jan W.: Cyclization of Propargylic Amides: Mild Access to Oxazole Derivatives. Chemistry - A European Journal 2010, 16, 956. <http://dx.doi.org/10.1002/chem.200902472>
  • Barluenga Jose: ChemInform Abstract: Transferring Iodine: More than a Simple Functional Group Exchange in Organic Synthesis. ChemInform 2010, 30, no. <http://dx.doi.org/10.1002/chin.199950269>
  • Rajender Reddy K., Venkateshwar M., Uma Maheswari C., Santhosh Kumar P.: Mild and efficient oxy-iodination of alkynes and phenols with potassium iodide and tert-butyl hydroperoxide. Tetrahetron Lett 2010, 51, 2170. <http://dx.doi.org/10.1016/j.tetlet.2010.02.074>
  • Hashmi A. Stephen K., Ramamurthi Tanuja Dondeti, Rominger Frank: Synthesis, structure and reactivity of organogold compounds of relevance to homogeneous gold catalysis. J Organomet Chem 2009, 694, 592. <http://dx.doi.org/10.1016/j.jorganchem.2008.11.054>
  • Montaña Ángel M., Barcia Juan A., Kociok-Köhn Gabriele, Font-Bardía Mercè: Synthesis of 2,6-dioxatricyclo[3.3.1.03,7]nonanes by intramolecular haloetherification and/or transannular hydroxycyclization of alkenes in [4+3]-cycloadducts. Tetrahed 2009, 65, 5308. <http://dx.doi.org/10.1016/j.tet.2009.04.076>
  • Stavber Gaj, Iskra Jernej, Zupan Marko, Stavber Stojan: Aerobic Oxidative Iodination of Organic Compounds with Iodide Catalyzed by Sodium Nitrite. Adv Synth Catal 2008, 350, 2921. <http://dx.doi.org/10.1002/adsc.200800553>
  • Muñiz Kilian, Hövelmann Claas H., Campos-Gómez Esther, Barluenga José, González José M., Streuff Jan, Nieger Martin: Intramolecular Diamination of Alkenes with Palladium(II)/Copper(II) Bromide and IPy2BF4: The Role of Halogenated Intermediates. Chem Asian J 2008, 3, 776. <http://dx.doi.org/10.1002/asia.200700373>
  • López J. Cristóbal, Bernal-Albert Paloma, Uriel Clara, Gómez Ana M.: Ready Transformation of Partially Unprotected Thioglycosides into Glycosyl Fluorides Mediated by NIS/HF-Pyridine or Et3N·3HF. Eur J Org Chem 2008, 2008, 5037. <http://dx.doi.org/10.1002/ejoc.200800754>
  • Bietti Massimo, Lanzalunga Osvaldo, Salamone Michela: Involvement of alkoxyl radical intermediates in the photolysis of 1-alkylcycloalkanols in the presence of bis(pyridine)iodonium tetrafluoroborate. J Photochem Photobiol A Chem 2006, 182, 33. <http://dx.doi.org/10.1016/j.jphotochem.2006.01.008>
  • Midorikawa Koji, Suga Seiji, Yoshida Jun-ichi: Selective monoiodination of aromatic compounds with electrochemically generated I+ using micromixing. Chem Commun 2006, 3794. <http://dx.doi.org/10.1039/b607284d>
  • Barluenga José, García-García Patricia, Fernández-Rodríguez Manuel A., Aguilar Enrique, Merino Isabel: Lithium Benzocyclobuteneoxide as a Precursor of a Vinylogous Enolate: Solvent-Controlled Synthesis of Highly Functionalized Seven-Membered Benzocarbocycles. Angew Chem 2005, 117, 6025. <http://dx.doi.org/10.1002/ange.200501468>
  • Barluenga José, García-García Patricia, Fernández-Rodríguez Manuel A., Aguilar Enrique, Merino Isabel: Lithium Benzocyclobuteneoxide as a Precursor of a Vinylogous Enolate: Solvent-Controlled Synthesis of Highly Functionalized Seven-Membered Benzocarbocycles. Angew Chem Int Ed 2005, 44, 5875. <http://dx.doi.org/10.1002/anie.200501468>
  • Álvarez-Pérez Mónica, Rodríguez Félix, Fañanás Francisco J.: IPy2BF4-Mediated Rearrangements of 1,2-Difunctionalized Compounds and Olefins. Chem Eur J 2005, 11, 5938. <http://dx.doi.org/10.1002/chem.200500070>
  • Urankar Damijana, Rutar Irena, Modec Barbara, Dolenc Darko: Synthesis of Bromo- and Iodohydrins from Deactivated Alkenes by Use ofN-Bromo- andN-Iodosaccharin. Eur J Org Chem 2005, 2005, 2349. <http://dx.doi.org/10.1002/ejoc.200400829>
  • Cid José, Alonso José M., Andrés José I., Fernández Javier, Gil Pilar, Iturrino Laura, Matesanz Encarna, Meert Theo F., Megens Anton, Sipido Victor K.: Synthesis and structure–activity relationship of 2-(aminoalkyl)-3,3a,8,12b-tetrahydro-2H-dibenzocyclohepta[1,2-b]furan derivatives: a novel series of 5-HT2A/2C receptor antagonists. Biorg Med Chem Lett 2004, 14, 2765. <http://dx.doi.org/10.1016/j.bmcl.2004.03.069>
  • Trabanco Andrés Avelino, Alonso José Manuel, Andrés José Ignacio, Cid José Maria, Fernández Javier, Iturrino Laura, Megens Anton: Synthesis of 2-N,N-Dimethylaminomethyl-2,3,3a,12b-tetrahydrodibenzo-[b,f]furo[2,3-d]oxepin Derivatives as Potential Anxiolytic Agents. Chem Pharm Bull 2004, 52, 262. <http://dx.doi.org/10.1248/cpb.52.262>
  • Jereb Marjan, Stavber Stojan, Zupan Marko: Direct iodination of indanone and tetralone derivatives by elemental iodine activated by Selectfluor™ F-TEDA-BF4. Tetrahedron 2003, 59, 5935. <http://dx.doi.org/10.1016/S0040-4020(03)00904-9>
  • Dolenc Darko: Iodination of Enol Acetates and 1,3-Diones Using N-Iodosaccharin. Synth Common 2003, 33, 2917. <http://dx.doi.org/10.1081/SCC-120022182>
  • Barluenga José, González-Bobes Francisco, Ananthoju Sreenivasa R., García-Martín Miguel A., González José M.: Die oxidative Öffnung von Cycloalkanolen: ein effizienter Zugang zuω-Iodcarbonylverbindungen. Angew Chem 2001, 113, 3491. <http://dx.doi.org/10.1002/1521-3757(20010917)113:18<3491::AID-ANGE3491>3.0.CO;2-U>
  • Barluenga José, González-Bobes Francisco, Ananthoju Sreenivasa R., García-Martín Miguel A., González José M.: Oxidative Opening of Cycloalkanols: An Efficient Entry toω-Iodocarbonyl Compounds. Angew Chem Int Ed 2001, 40, 3389. <http://dx.doi.org/10.1002/1521-3773(20010917)40:18<3389::AID-ANIE3389>3.0.CO;2-V>
  • González M.C., del Val J.J., Zamora F.: Inclusion of the cation iodonium (I3+) into the structure of poly(N-vinylcarbazole). Poly 2001, 42, 9735. <http://dx.doi.org/10.1016/S0032-3861(01)00490-6>