Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 12
238
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Ionic Liquid Oxidant for Efficient and Selective Oxidation of Benzylic Alcohols

, , &
Pages 1725-1732 | Received 26 Jan 2010, Published online: 29 Apr 2011

REFERENCES

  • Trost , B. M. In Comprehensive Organic Synthesis (Oxidation) ; S. V. Ley (Ed.); Pergamon : New York , 1991 ; vol. 17 , p. 260 .
  • Einhorn , J. ; Einhorn , C. ; Ratajczak , F. ; Pierre , J. L. Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts . J. Org. Chem. 1996 , 61 , 7452 – 7454 .
  • Muzrt , J. ; Ajjou , A. N. A. ; Ait-Mohand , S. Effective chromium-mediated oxidation of allylic and benzylic alcohols by sodium percarbonate . Tetrahedrone Lett. 1994 , 35 , 1989 – 1990 .
  • Lee , R. A. ; Donald , D. S. Magtrieve, an efficient, magnetically retrievable, and recyclable oxidant . Tetrahedrone Lett. 1997 , 38 , 3857 – 3860 .
  • Patel , S. ; Mishra , B. K. Chromium(VI) oxidants having quaternary ammonium ions: Studies on synthetic applications and oxidation kinetics . Tetrahedron 2007 , 63 , 4367 – 4406 .
  • Lan , Y. ; Deng , B. ; Kim , C. ; Thornton , E. C. ; Xu , H. Catalysis of elemental sulfur nanoparticles on chromium(VI) reduction by sulfide under anaerobic conditions . Environ. Sci. Technol. 2005 , 39 , 2087 – 2094 .
  • Corey , E. J. ; Suggs , J. W. Pyridinium chlorochromate: An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett. 1975, 16, 2647–2650.
  • Guziec , F. S. ; Luzzio , F. A. The oxidation of alcohols using 2,2′-bipyridinium chlorochromate . Synthesis 1980 , 691 – 693 .
  • Kim , S. ; Lhim , D. C. Imidazolium dichromate: A new reagent for the oxidation of alcohols to carbonyl compounds . Bull. Chem. Soc. Jpn. 1986 , 59 , 3297 – 3298 .
  • (a) Hosseinzadeh , R. ; Tajbakhsh , M. ; Niaki , M. Y. 2,6-Dicarboxypyridinium chlorochromate: A mild, efficient, and selective reagent for oxidative deprotection of oximes to carbonyl compounds . Tetrahedron Lett. 2002 , 43 , 9413 – 9416 ; (b) Hosseinzadeh , R. ; Tajbakhsh , M. ; Shakoori , A. ; Niaki , M. Y. 2,6-Dicarboxypyridinium chlorochromate: An efficient and selective reagent for the mild deprotection of acetals, thioacetals, and 1,1-diacetates to carbonyl compounds . Monatsh. Chem. 2004 , 135 , 1243 – 1249 ; (c) Tajbakhsh , M. ; Hosseinzadeh , R. ; Shakoori , A. 2,6-Dicarboxypyridinium chlorochromate: An efficient and selective reagent for the oxidation of thiols to disulfides and sulfides to sulfoxides . Tetrahedron Lett. 2004 , 45 , 1889 – 1893 .
  • (a) Tajbakhsh , M. ; Hosseinzadeh , R. ; Sadatshahabi , M. Synthesis and application of 2,6-dicarboxypyridinium fluorochromate as a new solid-phase oxidant . Synth. Commun. 2005 , 35 , 1547 – 1554 ; (b) Tajbakhsh , M. ; Hosseinzadeh , R. ; Ramezanian-Lehmali , F. ; Sadatshahabi , M. 2,6-Dicarboxypyridinium fluorochromate: A mild and efficient reagent for oxidative deprotection of oximes, phenylhydrazones, and semicarbazones to their corresponding carbonyl compounds under solvent-free conditions . J. Chin. Chem. Soc. 2005 , 52 , 1005 – 1010 .
  • Kim , S. ; Chang , H. 1-Methylimidazolium chlorochromate: A new efficient oxidizing agent for oxidation of alcohols and oxidative cleavage of oximes . Bull. Korean Chem. Soc. 1987 , 8 , 183 – 185 .
  • Martinez , Y. ; Delasheras , M. A. ; Vaquero , J. J. ; Garcianavio , J. L. ; Alvarezbuilla , J. 1-(Benzoylamino)-3-methylimidazolium chlorochromate (BAMICC), a new selective and mild reagent for the oxidation of allylic and benzylic alcohols . Tetrahedron Lett. 1995 , 36 , 8513 – 8516 .
  • (a) Welton , T. Room-temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 – 2083 ; (b) Wasserscheid , P. ; Keim , W. Ionic liquids—New “solutions” for transition-metal catalysis . Angew. Chem. Int. Ed. 2000 , 39 , 3772 – 3789 ; (c) Sheldon , R. Catalytic reactions in ionic liquids . Chem. Commun. 2001 , 2399 – 2407 .
  • (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) Huddleston , 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 .
  • Dyson , P. J. ; Ellis , D. J. ; Parker , D. G. ; Welton , T. Arene hydrogenation in a room-temperature ionic liquid using a ruthenium cluster catalyst . Chem. Commun. 1999 , 25 – 26 .
  • Stark , A. ; MacLean , B. L. ; Singer , R. D. 1-Ethyl-3-methyl imidazolium halogenoaluminate ionic liquids as solvents for Friedel–Crafts acylation reactions of ferrocene . J. Chem. Soc., Dalton Trans. 1999 , 63 – 66 .
  • Fisher , T. ; Sethi , A. ; Welton , T. ; Woolf , J. Diels–Alder reaction in room-temperature ionic liquids . Tetrahedron Lett. 1999 , 40 , 793 – 796 .
  • Bohm , V. P. W. ; Herrmann , W. A. Nonaqueous ionic liquids: Superior reaction media for the catalytic Heck-vinylation of chloroarenes . Chem. Eur. J. 2000 , 6 , 1017 – 1025 .
  • Judeh , Z. M. A. ; Ching , C. B. ; Bu , J. ; McCluskey , A. The first Bischler–Napieralski cyclization in a room temperature ionic liquid . Tetrahedron Lett. 2002 , 43 , 5089 – 5091 .
  • Ellis , B. ; Keim , W. ; Wasserscheid , P. Linear dimerisation of but-1-ene in biphasic mode using buffered chloroaluminate ionic liquid solvents . Chem. Commun. 1999 , 337 – 338 .
  • Miyaura , N. ; Suzuki , A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457–2483.
  • Olivier , H. Recent developments in the use of non-aqueous ionic liquids for two-phase catalysis . J. Mol. Cat. A: Chem. 1999 , 146 , 285 – 289 .
  • (a) Shen , H. Y. ; Judeh , Z. M. A. ; Ching , C. B. Selective alkylation of phenol with tert-butyl alcohol catalyzed by [bmim]PF6 . Tetrahedron Lett. 2003 , 44 , 981 – 983 ; (b) Shen , H. Y. ; Judeh , Z. M. A. ; Ching , C. B. ; Xia , Q. H. Comparative studies on alkylation of phenol with tert-butyl alcohol in the presence of ionic or solid acid catalysts in ionic liquids . J. Mol. Cat. A: Chem. 2004 , 212 , 301 – 308 .
  • (a) Zhao , H. ; Malhotra , S. V. Applications of ionic liquids in organic synthesis . Aldrichim. Acta 2002 , 35 , 75 – 83 ; (b) Dupont , J. ; De Souza , R. F. ; Suarez , P. A. Z. Ionic liquid (molten salt) phase organometallic catalysis . Chem. Rev. 2002 , 102 , 3667 – 3692 .
  • (a) Zheng , Y. ; Du , X. ; Bao , W. Selective oxidation of primary and secondary alcohols with chromium trioxide in ionic liquid . J. Chem. Res. 2005 , 12 , 753 – 754 ; (b) Mehdi , H. ; Bodor , A. ; Lantos , D. ; Horvath , I. T. ; Vos , D. E. D. ; Binnemans , K. Imidazolium ionic liquids as solvents for cerium(IV)-mediated oxidation reactions . J. Org. Chem. 2007 , 72 , 517 – 524 .
  • Liu , Z. ; Chen , Z. ; Zheng , Q. Mild oxidation of alcohols with o-iodoxybenzoic acid (IBX) in ionic liquid 1-butyl-3-mehyl-imidazolium chloride and water . Org. Lett. 2003 , 5 , 3321 – 3323 .
  • Shaabani , A. ; Farhangi , E. ; Rahmati , A. Aerobic oxidation of alkyl arenes and alcohols using cobalt(II) phthalocyanine as a catalyst in 1-buthyl-3-methyl-imidazolium bromide . Appl. Catal. A: Gen. 2008 , 338 , 14 – 19 .
  • Wu , X. E. ; Ma , L. ; Ding , M. X. ; Gao , L. X. Imidazolium ionic liquid-grafted 2,2′-bipyridine: A novel ligand for the recyclable copper-catalyzed selective oxidation of alcohols in ionic liquid [bmim][PF6] . Chem. Lett. 2005 , 34 , 312 .
  • Chhikara , B. S. ; Chandra , R. ; Tandon , V. Oxidation of alcohols with hydrogen peroxide catalyzed by a new imidazolium ion–based phosphotungstate complex in ionic liquid . J. Catal. 2005 , 230 , 436 – 439 .
  • (a) Heidarizadeh , F. ; Asareh , H. Simple oxidation of benzylic halides with 1-buthyl-3-methyl imidazolium periodate . Asian J. Chem. 2009 , 21 , 949 – 952 ; (b) Heidarizadeh , F. ; Allahverdi , G. Study of oxidant ionic liquid with the help of soluble support . Asian J. Chem. 2008 , 20 , 2822 – 2826 .
  • 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 .
  • Skoog , D. A. ; West , D. M. ; Holler , F. J. Fundamentals of Analytical Chemistry, , 5th ed. ; Saunders College : New York , 1988 .
  • Tajbakhsh , M. ; Ghaemi , M. ; Sarabi , S. ; Ghasemzadeh , M. ; Heravi , M. M. N-Methyl piperidinium chlorochromate adsorbed on alumina: A new and selective reagent for the oxidation of benzylic alcohols to their corresponding carbonyl compounds . Monatsh. Chem. 2000 , 131 , 1213 – 1216 .
  • Surendra , K. ; Srilakshmi Krishnaveni , N. ; Arjun Reddy , M. ; Nageswar , Y. V. D. ; Rama Rao , K. Mild oxidation of alcohols with o-iodoxybenzoic acid (IBX) in water/acetone mixture in the presence of β-cyclodextrin . J. Org. Chem. 2003 , 68 , 2058 – 2059 .
  • Pouchert , C. J. The Aldrich Library of NMR Spectra, , 2nd ed. ; Aldrich Chemical Company : Milwaukee , WI , 1983 ; vol. 2 .
  • Bhar , S. ; Ghaudhuri , S. K. Remarkable reactivity of pyridinium chlorochromate adsorbed on neutral alumina under solvent-free conditions . Tetrahedron 2003 , 59 , 3493 – 3498 .
  • Kasmai , H. S. ; Mischke , S. G. ; Blake , T. J. 18-Crown-6 complexes of n-buthylammonium and pyridinium chlorochromates: Mild and selective oxidizing agents for alcohols . J. Org. Chem. 1995 , 60 , 2267 – 2270 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.