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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 21
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Original Articles

Ionic Liquid Iodinating Reagent for Mild and Efficient Iodination of Aromatic and Heteroaromatic Amines and Terminal Alkynes

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Pages 2913-2925 | Received 23 Jul 2012, Published online: 25 Jul 2013

REFERENCES

  • De Meijere , A. ; Diederich , F. (Eds.). Metal-Catalyzed Cross-Coupling Reactions, , 2nd ed. ; Wiley-VCH : Weinheim , Germany , 2004 .
  • (a) Yao , Q. ; Kinney , E. P. ; Yang , Z. Ligand-free Heck reaction: Pd(OAc)2 as an active catalyst revisited . J. Org. Chem. 2003 , 68 , 7528 – 7531 ; (b) Seyferth , D. The Grignard reagents . Organometallics 2009 , 28 , 1598 – 1605 .
  • (a) Nicolaou , K. C. The battle of calicheamicin γI . Angew. Chem., Int. Ed. Engl. 1993 , 32 , 1377 – 1385 ; (b) Tedder , J. M. ; Nechvatal , A. ; Murray , A. W. ; Carnduff , J. Basic Organic Chemistry; vol. 4; John Wiley & Sons: London, 1971; chapter 3 .
  • Merkushev , E. B. Advances in the synthesis of iodoaromatic compounds . Synthesis 1988 , 10 , 923 – 937 .
  • (a) Mattern , D. L. Direct aromatic periodination . J. Org. Chem. 1984 , 49 , 3051 – 3053 ; (b) Lulinski , P. ; Skulski , L. Iodination of both deactivated and activated arenes with sodium periodate or sodium iodate as the oxidants . Bull. Chem. Soc. Jpn. 2000 , 73 , 951 – 956 ; (c) Suzuki , H. ; Nakamura , K. ; Goto , R. The direct iodination of polyalkylbenzenes bearing bulky groups . Bull. Chem. Soc. Jpn. 1966 , 39 , 128 – 131 .
  • (a) Pasha , M. A. ; Myint , Y. Y. Acid-catalysed selective monoiodination of electron-rich arenes by alkali metal iodides . Synth. Commun. 2004 , 34 , 2829 – 2833 ; (b) Abderrazak , B. ; Francisco , F. ; Miguel , Y. Aromatic iodination with the I2-HgX2 combination . Tetrahedron 1994 , 50 , 5139 – 5146 ; (c) Sy , W. ; Lodge , B. ; By , A. Aromatic iodination with iodine and silver sulfate . Synth. Commun. 1990 , 20 , 877 – 880 .
  • Johnsson , R. ; Meijer , A. ; Ellervik , U. Mild and efficient direct aromatic iodination . Tetrahedron 2005 , 61 , 11657 – 11663 .
  • Kosynkin , D. V. ; Tour , J. M. Benzyltriethylammonium dichloroiodate/sodium bicarbonate combination as an inexpensive, environmentally friendly, and mild iodinating reagent for anilines . Org. Lett. 2001 , 3 , 991 – 992 .
  • (a) Kajigaeshi , S. ; Kakinami , T. ; Watanabe , F. ; Okamoto , T. Halogenation using quaternary ammonium polyhalides, XVII: Iodination of acetanilide derivatives with benzyltrimethylammonium dichloroiodate and zinc chloride. Bull. Chem. Soc. Jpn. 1989, 62, 1349–1351; (b) Kajigaeshi , S. ; Kakinami , T. ; Moriwaki , M. ; Watanabe , M. ; Fujisaki , S. ; Okamoto , T. Iodination of aromatic ethers by use of benzyltrimethylammonium dichloroiodate and zinc chloride. Chem. Lett. 1988, 795–798; (c) Kajigaeshi , S. ; Kakinami , T. ; Yamasaki , H. ; Fujisaki , S. ; Okamoto , T. Halogenation using quaternary ammonium polyhalides, VII. Iodination of aromatic amines by use of benzyltrimethylammonium dichloroiodate. Bull. Chem. Soc. Jpn. 1988, 61, 600–602; (d) Tilve , R. D. ; Kanetkar , V. R. Regioselective iodination of activated arenes using phenyl trimethylammonium dichloroiodate in ionic liquid under microwave irradiation. Synth. Commun. 2005, 35, 1313–1318; (e) Kajigaeshi , S. ; Kakinami , T. ; Yamasaki , H. ; Fujisaki , S. ; Kondo , M. ; Okamoto , T. Iodination of phenols by use of benzyltrimethylammonium dichloroiodate. Chem. Lett. 1987, 2109–2112; (f) Okamoto , T. ; Kakinami , T. ; Fujimoto , H. ; Kajigashi , S. Halogenation using quaternary ammonium polyhalides, XXXI: Halogenation of thiophene derivatives with benzyltrimethylammonium polyhalides. Bull. Chem. Soc. Jpn. 1991, 64, 2566–2568; (g) Custelceanu , R. ; Vlassa , M. ; Silberg , I. A. Reaction of π-deficient aromatic heterocycles with ammonium polyhalides, III: Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides. Monatsh. Chem. 1997, 128, 919–925; (h) Wariishi , K. ; Morishima , S. I. ; Inagaki , Y. A facile synthesis of 1,4-dialkoxy-2,5-diiodobenzenes: Reaction of dialkoxybenzenes with iodine monochloride in alcoholic solvents. Org. Process Res. Dev. 2003, 7, 98–100.
  • Filimonov , V. D. ; Semenischeva , N. S. ; Krasnokutskaya , E. A. ; Hwang , H. Y. ; Chi , K. W. Tetraalkylammonium dichloroiodates as iodinating agents: Absence of activity in solid phases and superelectrophilic activity in sulfuric acid . Synthesis 2008 , 401 – 404 .
  • Mitra , S. S. ; Sreekumar , K. Polyhalide derivatives of poly[N-(2-aminoethyl)-acrylamido]triethylammonium resins as iodinating reagents . Macromol. Chem. Phys. 1997 , 198 , 1611 – 1621 .
  • (a) Burli , R. ; Vasella , A. Oligosaccharide analogues of polysaccharides, part 14: Carbocyclic cyclodextrin analogues: Synthesis of all trimeric and tetrameric isomers by homo- and heterocoupling of 1,4-cis-diethynylated 1,5-anhydroglucitols . Helv. Chim. Acta 1997 , 80 , 2215 – 2237 ; (b) Nantz , M. H. ; Moss , D. K. ; Spence , J. D. ; Olmstead , M. M. Actuating cycloaromatization of a bicyclo[7.3.1]enediyne by annelation: An example of inverse dependence on bridge atom hybridization . Angew. Chem., Int. Ed. Engl. 1998 , 37 , 470 – 473 ; (c) Luithle , J. E. A. ; Pietruszka , J. Synthesis of enantiomerically pure cis-cyclopropylboronic esters . Eur. J. Org. Chem. 2000 , 2557 – 2562 ; (d) Kunishima , M. ; Nakata , D. ; Tanaka , S. ; Hioki , K. ; Tani , S. Generation and reactions of alkynylsamariums . Tetrahedron 2000 , 56 , 9927 – 9935 ; (e) Damle , S. V. ; Seomoon , D. ; Lee , P. H. Palladium-catalyzed homocoupling reaction of 1-iodoalkynes: A simple and efficient synthesis of symmetrical 1,3-diynes . J. Org. Chem. 2003 , 68 , 7085 – 7087 .
  • (a) Joubert , N. ; Amblard , F. ; Rapp , K. L. ; Schinazi , R. F. ; Agrofoglio , L. A. Synthesis and anti-HIV activity of 5-haloethynyl and 5-(1,2-dihalo)vinyl analogues of AZT and FLT . Tetrahedron 2008 , 64 , 4444 – 4452 ; (b) Kabalka , G. W. ; Shoup , T. M. ; Goodman , M. M. Synthesis and evaluation of a new series of 17α -[123I]iodovinyl estradiols . Nucl. Med. Biol. 2000 , 27 , 279 – 287 ; (c) Jeffery , T. Copper(I)- and phase-transfer-catalysed iodination of terminal alkynes . J. Chem. Soc., Chem. Commun. 1988 , 909 – 910 .
  • Vaughn , T. H. ; Nieuwland , J. A. Iodination in liquid ammonia . J. Am. Chem. Soc. 1932 , 54 , 787 – 791 .
  • Meng , L. G. ; Cai , P. J. ; Guo , Q. X. ; Xue , S. Direct iodination of monosubstituted aryl acetylenes and acetylenic ketones . Synth. Commun. 2008 , 38 , 225 – 231 .
  • Reddy , K. R. ; Venkateshwar , M. ; Maheswari , C. U. ; Kumar , P. S. Mild and efficient oxy-iodination of alkynes and phenols with potassium iodide and tert-butyl hydroperoxide . Tetrahedron Lett. 2010 , 51 , 2170 – 2173 .
  • Chen , S. N. ; Hung , T. T. ; Lin , T. C. ; Tsai , F. Y. Reusable and efficient CuI/TBAB-catalyzed iodination of terminal alkynes in water under air . J. Chin. Chem. Soc. 2009 , 56 , 1078 – 1081 .
  • Yan , J. ; Li , J. ; Cheng , D. Novel and efficient synthesis of 1-iodoalkynes . Synlett 2007 , 2442 – 2444 .
  • Stefani , H. A. ; Cella , R. ; Dorr , F. A. ; Pereira , C. M. P. ; Gomes , F. P. ; Zeni , G. Ultrasound-assisted synthesis of functionalized arylacetylenes . Tetrahedron Lett. 2005 , 46 , 2001 – 2003 .
  • Ricci , A. ; Taddei , M. ; Dembech , P. ; Guerrini , A. ; Seconi , G. Reactions of terminal alkynes with bis(trimethylsilyl) peroxide and zinc(II) iodide: A convenient method for the preparation of 1-iodo-1-alkynes . Synthesis 1989 , 461 – 463 .
  • Barluenga , J. ; Gonzalez , J. M. ; Rodriguez , M. A. ; Campos , P. J. ; Asensio , G. An improved method for the synthesis of 1-iodoalkynes. Synthesis 1987, 661–662.
  • Casarini , A. ; Dembech , P. ; Reginato , G. ; Ricci , A. ; Seconi , G. Terminal 1-halo- and 1-pseudohalo-1-alkynes via bis(trimethylsilyl)peroxide (BTMSPO)–promoted umpolung transfer of halides and pseudohalides . Tetrahedron Lett. 1991 , 32 , 2169 – 2170 .
  • Brunel , Y. ; Rousseau , G. An easy preparation of iodoacetylenes . Tetrahedron Lett. 1995 , 36 , 2619 – 2622 .
  • Nishikawa , T. ; Shibuya , S. ; Hosokawa , S. ; Isobe , M. One-pot synthesis of haloacetylenes from trimethylsilylacetylenes . Synlett 1994 , 485 – 486 .
  • Kabalka , G. W. ; Mereddy , A. R. Iodination of organotrifluoroborates: Synthesis of vinyl and alkynyl iodides . Tetrahedron Lett. 2004 , 45 , 1417 – 1419 .
  • Abe , H. ; Suzuki , H. Copper-mediated nucleophilic displacement reactions of 1-haloalkynes: Halogen–halogen exchange and sulfonylation . Bull. Chem. Soc. Jpn. 1999 , 72 , 787 – 798 .
  • Naskar , D. ; Roy , S. 1-Haloalkynes from propiolic acids: A novel catalytic halodecarboxylation protocol . J. Org. Chem. 1999 , 64 , 6896 – 6897 .
  • (a) Earle , M. J. ; Seddon , K. R. Ionic liquids: Green solvents for the future . Pure Appl. Chem. 2000 , 72 , 1391 – 1398 ; (b) Wasserscheid , P. ; Keim , W. Ionic liquids—New “solutions” for transition-metal catalysis . Angew. Chem., Int. Ed. 2000 , 39 , 3772 – 3789 ; (c) Olivier-Bourbigou , H. ; Magna , L. Ionic liquids: Perspectives for organic and catalytic reactions . J. Mol. Cat. A: Chem. 2002 , 182–183 , 419 – 437 ; (d) Davis , J. H. ; Fox , P. A. From curiosities to commodities: Ionic liquids begin the transition . Chem. Commun. 2003 , 1209 – 1212 ; (e) Sheldon , R. A. Green solvents for sustainable organic synthesis: state of the art . Green Chem. 2005 , 7 , 267 – 278 .
  • (a) Welton , T. Room-temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 – 2083 ; (b) Zhao , H. ; Malhotra , S. V. Aldrichim. Acta 2002 , 35 , 75 – 83 ; (c) Jain , N. ; Kumar , A. ; Chauhan , S. ; Chauhan , S. M. S. Chemical and biochemical transformations in ionic liquids . Tetrahedron 2005 , 61 , 1015 – 1060 ; (d) Borodkin , G. I. ; Shubin , V. G. Electrophilic reactions of aromatic and heteroaromatic compounds in ionic liquids . Russ. J. Org. Chem. 2006 , 42 , 1745 – 1770 ; (e) Jorapur , Y. R. ; Chi , D. Y. Ionic liquids: An environmentally friendly media for nucleophilic substitution reactions . Bull. Korean Chem. Soc. 2006 , 27 , 345 – 354 .
  • (a) Hapiot , P. ; Lagrost , C. Electrochemical reactivity in room-temperature ionic liquids . Chem. Rev. 2008 , 108 , 2238 – 2264 ; (b) Arvai , R. ; Toulgoat , F. ; Medebielle , M. ; Langlois , B. ; Alloin , F. ; Iojoiu , C. ; Sanchez , J. Y. New aryl-containing fluorinated sulfonic acids and their ammonium salts, useful as electrolytes for fuel cells or ionic liquids . J. Fluor. Chem. 2008 , 129 , 1029 – 1035 .
  • (a) Blanchard , L. A. ; Brennecke , J. F. Recovery of organic products from ionic liquids using supercritical carbon dioxide . Ind. Eng. Chem. Res. 2001 , 40 , 287 – 292 ; (b) Hoddleston , J. G. ; Willauer , H. D. ; Rogers , R. D. Room-temperature ionic liquids as novel media for “clean” liquid–liquid extraction . Chem. Commun. 1998 , 1765 – 1766 .
  • (a) Sheldon , R. Catalytic reactions in ionic liquids . Chem. Commun. 2001 , 2399 – 2407 ; (b) Dupont , J. ; De Souza , R. F. ; Suarez , P. A. Z. Ionic liquid (molten salt) phase organometallic catalysis . Chem. Rev. 2002 , 102 , 3667 – 3692 ; (c) Parvulescu , V. I. ; Hardacre , C. Catalysis in ionic liquids . Chem. Rev. 2007 , 107 , 2615 – 2665 .
  • (a) Chiappe , C. ; Pieraccini , D. Regioselective iodination of arenes in ionic liquids mediated by SelectfluorTM reagent F-TEDA-BF4. Arkivoc 2002, 11, 249–255; (b) Pavlinac , J. ; Laali , K. K. ; Zupan , M. ; Stavber , S. Iodination of organic compounds with elemental iodine in the presence of hydrogen peroxide in ionic liquid media. Aust. J. Chem. 2008, 61, 946–955; (c) Bhilare , S. V. ; Deorukhkar , A. R. ; Darvatkar , N. B. ; Salunkhe , M. M. Regioselective iodination of arenes using iodine/NaBO3 · 4H2O system in ionic liquid. Synth. Commun. 2008, 38, 2881–2888; (d) Hubbard , A. ; Okazaki , T. ; Laali , K. K. Halo- and azidodediazoniation of arenediazonium tetrafluoroborates with trimethylsilyl halides and trimethylsilyl azide and Sandmeyer-type bromodediazoniation with Cu(I)Br in [BMIM][PF6] ionic liquid. J. Org. Chem. 2008, 73, 316–319; (e) Tilve , R. D. ; Kanetkar , V. R. Regioselective iodination of activated arenes using phenyl trimethylammonium dichloroiodate in ionic liquid under microwave irradiation. Synth. Commun. 2005, 35, 1313–1318; (f) Meshram , H. M. ; Reddy , P. N. ; Vishnu , P. ; Sadashiv , K. ; Yadav , J. S. A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides in ionic liquids. Tetrahedron Lett. 2006, 47, 991–995; (g) Yadav , J. S. ; Reddy , B. V. S. ; Reddy , P. S. R. ; Basak , A. K. ; Narsaiah , A. V. Efficient halogenation of aromatic systems using N-halosuccinimides in ionic liquids. Adv. Synth. Catal. 2004, 346, 77–82.
  • (a) Hosseinzadeh , R. ; Mohadjerani , M. ; Tajbakhsh , M. ; Nouzarian , M. Ionic liquid oxidant for efficient and selective oxidation of benzylic alcohols . Synth. Commun. 2011 , 41 , 1725 – 1732 ; (b) Ranu , B. C. ; Banerjee , S. Ionic liquid as reagent. A green procedure for the regioselective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst- and solvent-free conditions . J. Org. Chem. 2005 , 70 , 4517 – 4519 ; (c) Leadbeater , N. E. ; Torenius , H. M. ; Tye , H. Ionic liquids as reagents and solvents in conjunction with microwave heating: Rapid synthesis of alkyl halides from alcohols and nitriles from aryl halides . Tetrahedron 2003 , 59 , 2253 – 2258 .
  • (a) Ranu , B. C. ; Adak , L. ; Banerjee , S. Halogenation of carbonyl compounds by an ionic liquid, [AcMIm]X, and ceric ammonium nitrate (CAN) . Aust. J. Chem. 2007 , 60 , 358 – 362 ; (b) Bortolini , O. ; Bottai , M. ; Chiappe , C. ; Conte , V. ; Pieraccini , D. Trihalide-based ionic liquids. Reagent-solvents for stereoselective iodination of alkenes and alkynes . Green Chem. 2002 , 4 , 621 – 627 ; (c) Cristiano , R. ; Ma , K. ; Pottanat , G. ; Weiss , R. G. Tetraalkylphosphonium trihalides: Room temperature ionic liquids as halogenation reagents . J. Org. Chem. 2009 , 74 , 9027 – 9033 .
  • (a) Hosseinzadeh , R. ; Tajbakhsh , M. ; Mohadjerani , M. ; Lasemi , Z. Efficient and regioselective bromination of aromatic compounds with ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB) . Synth. Commun. 2010 , 40 , 868 – 876 ; (b) Hosseinzadeh , R. ; Tajbakhsh , M. ; Mohadjerani , M. ; Lasemi , Z. Ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB): An efficient reagent for the monobromination of 1,3-diketones and β-ketoesters . Monatsh. Chem. 2009 , 140 , 57 – 60 ; (c) Hosseinzadeh , R. ; Tajbakhsh , M. ; Khaledi , H. Ethylenebis(N-methylimidazolium) chlorochromate (EBMICC): A new selective and mild reagent for oxidation of alcohols, hydroquinones, and trimethylsilyl ethers . J. Chin. Chem. Soc. 2008 , 55 , 239 – 243 ; (d) Hosseinzadeh , R. ; Tajbakhsh , M. ; Khaledi , H. ; Ghodrati , K. Ethylenebis(N-methylimidazolium) chlorochromate (EBMICC): An efficient and selective reagent for the oxidation of thiols to disulfides . Monatsh. Chem. 2007 , 138 , 871 – 873 .
  • Skoog , D. A. ; West , D. M. ; Holler , F. J. Fundamentals of Analytical Chemistry, , 5th ed. ; Saunders College Publishing : Philadelphia , 1988 .
  • (a) Srisook , E. ; Chi , D. Y. The syntheses of 3-substituted 4-(pyridin-2-ylthio)indoles via Leimgruber–Batcho indole synthesis . Bull. Korean Chem. Soc. 2004 , 25 , 895 – 899 ; (b) Cliff , M. D. ; Pyne , S. G. Synthesis of 4,4′-biimidazoles . Synthesis 1994 , 681 – 682 ; (c) Naidu , M. S. R. ; Bensusan , H. B. Reinvestigation of the orientation of halogen substitution in imidazoles by nuclear magnetic resonance spectroscopy . J. Org. Chem. 1968 , 33 , 1307 – 1309 ; (d) Panosyan , F. B. ; Still , I. W. J. An efficient route to 5-iodo-1-methylimidazole: Synthesis of xestomanzamine A . Can. J. Chem. 2001 , 79 , 1110 – 1114 ; (e) Fiumana , A. ; Jones , K. Intermolecular reactions of indol-2-yl radicals: A new route to 2-substituted indoles . Chem. Commun. 1999 , 1761 – 1762 ; (f) Russo , M. V. ; Lo Sterzo , C. ; Franceschini , P. ; Biagini , G. ; Furlani , A. Synthesis of highly ethynylated mono and dinuclear Pt(II) tethers bearing the 4,4′-bis(ethynyl)biphenyl (debp) unit as central core . J. Organomet. Chem. 2001 , 619 , 49 – 61 .

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