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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 5
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Original Articles

2,6-Dicarboxypyridinium Fluorochromate–Promoted Oxidation of Alkyl-Arenes into Carbonyl Compounds Under Nonaqueous and Aprotic Conditions

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Pages 678-685 | Received 25 Apr 2010, Published online: 01 Nov 2011

REFERENCES

  • (a) Warren , S. Organic Synthesis: The Disconnection Approach ; John Wiley and Sons : Singapore , 2004 ; p. 57 , 201, and 330; (b) Ghosh , S. ; Banik , B. K. ; Ghatak , U. R. An expeditious synthesis of 1,2,3,4-tetrahydro-1,1-dimethylphenanthrenes. J. Chem. Soc., Perkin Trans. 1. 1991, 3195–3197 .
  • Compere , D. ; Marazano , C. ; Das , B. C. An enantioselective access to lobelia alkaloids . J. Org. Chem. 1999 , 64 , 4528 – 4532 .
  • (a) Larock , R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations ; VCH : New York , 1989 ; p. 591 ; (b) Khan , A. T. ; Parvin , T. ; Choudhury , L. H. ; Ghosh , S. A simple synthetic protocol for oxidation of alkyl arenes into ketones using a combination of HBr–H2O2. Tetrahedron Lett. 2007, 48, 2271–2274; (c) Yamazaki , S. Chromium(VI) oxide–catalyzed benzylic oxidation with periodic acid. Org. Lett. 1999, 1, 2129–2132; (d) Choudary , B. M. ; Prasad , A. D. ; Bhuma , V. ; Swapna , V. Chromium-pillared clay as a catalyst for benzylic oxidation and oxidative deprotection of benzyl ethers and benzylamines: A simple and convenient procedure. J. Org. Chem. 1992, 57, 5841–5844 ; (e) Chidambaram , N. ; Chandrasekaran , S. tert-Butyl hydroperoxide-pyridinium dichromate: A convenient reagent system for allylic and benzylic oxidations. J. Org. Chem. 1987, 52, 5048–5051 .
  • Hosseinzadeh , R. ; Tajbakhsh , M. ; Vahedi , H. Selective oxidation of methylarenes with pyridinium chlorochromate . Synlett 2005 , 2769 – 2770 .
  • Kim , S. S. ; Sar , S. ; Tamrakar , P. Gif chemistry for oxidation of activated methylenes to ketones . Bull. Korean Chem. Soc. 2002 , 23 , 937 – 938 .
  • Murahashi , S. I. ; Komiya , N. ; Oda , Y. ; Kuwabara , T. ; Naota , T. Ruthenium-catalyzed oxidation of alkanes with tert-butyl hydroperoxide and peracetic acid . J. Org. Chem. 2000 , 65 , 9186 – 9193 .
  • Catino , A. J. ; Nichols , J. M. ; Choi , H. ; Gottipamula , S. ; Doyle , M. P. Benzylic oxidation catalyzed by dirhodium(II, III) caprolactamate . Org. Lett. 2005 , 23 , 5167 – 5170 .
  • Mohapatra , S. K. ; Selvam , P. A highly selective, heterogeneous route to enones from allylic and benzylic compounds over mesoporous CrMCM-41 molecular sieves . J. Catal. 2007 , 249 , 394 – 396 .
  • Badri , R. ; Soleymani , M. 3,6-Bis(triphenylphosphonium) cyclohexene peroxodisulfate as an efficient and mild oxidizing agent for conversion of alkylbenzenes to corresponding carbonyl compounds . Synth. Commun. 2002 , 32 , 2385 – 2389 .
  • Bonvin , Y. ; Callens , E. ; Larrosa , I. ; Henderson , D. A. ; Oldham , J. ; Burton , A. J. ; Barrett , A. G. M. Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide . Org. Lett. 2005 , 21 , 4549 – 4552 .
  • (a) Patel , S. ; Mishra , B. K. Chromium(VI) oxidants having quaternary ammonium ions: Studies on synthetic applications and oxidation kinetics . Tetrahedron 2007 , 63 , 4367 – 4406 ; (b) Tajbakhsh , M. ; Mohammadpoor-Baltork , I. ; Alimohammadi , K. An efficient and selective solid state oxidation of thiols to disulfides with quinolinium fluorochromate on silica gel . Monatsh Chem. 2003 , 134 , 1571 – 1575 ; (c) Tajbakhsh , M. ; Alimohammadi , K. ; Ramzanian Lehmali , F. ; Barghamadi , M. ; Shakeri , A. Quinolinium fluorochromate: An efficient and convenient reagent for oxidative cleavage of thioacetals to their parent carbonyl compounds . Phosphorus, Sulfur Silicon Relat. Elem. 2005 , 180 , 2587 – 2591 .
  • (a) Tajbakhsh , M. ; Hosseinzadeh , R. ; Yazdani-Niaki , M. Synthesis and application of 2,6-dicarboxypyridinium chlorochromate as a new oxidizing reagent for alcohols, silyl ethers, and THP ethers under mild and non-aqueous conditions. J. Chem. Res., Synop. 2002, 508–510; (b) Tajbakhsh , M. ; Hosseinzadeh , R. ; Yazdani-Niaki , M. 2,6-Dicarboxypyridinium chlorochromate: A mild, efficient, and selective reagent for oxidative deprotection of oximes to carbonyl compounds. Tetrahedron Lett. 2002, 43, 9413–9415; (c) Tajbakhsh , M. ; Hosseinzadeh , R. ; Ramzanian Lehmali , F. ; Sadatshahabi , M. 2,6-Dicarboxyopyridinium fluorochromate: A mild and efficient reagent for oxidative deprotection of oximes, phenylhydrazones to their corresponding carbonyl compounds under solvent-free conditions. J. Chin. Chem. Soc. 2005, 52, 1005–1009.
  • Hosseinzadeh , R. ; Tajbakhsh , M. ; Shakoori , A. R. ; Yazdani-Niaki , M. 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 .
  • (a) Tajbakhsh , M. ; Hosseinzadeh , R. ; Shakoori , A. R. 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 ; (b) Tajbakhsh , M. ; Mohammadpoor Baltork , I. ; Ramzanian Lehmali , F. Quinulinium fluorochromate C9H7NHCrO3F: An efficient and convenient reagent for the oxidative deprotection of trimethylsilyl ethers in nonaqueous conditions . Phosphorus, Sulfur Silicon Relat. Elem. 2003 , 178 , 2617 – 2620 ; (c) Tajbakhsh , M. ; Khazaei , A. ; Shabani Mahalli , M. ; Ghorbani Vaghi , R. N,N-Dibromobenzenesulfonamide as a reagent for oxidative cleavage of oximes to their parent carbonyl compounds under non-aqueous and aprotic conditions . J. Chem. Res., Synop. 2004 , 141 – 142 ; (d) Tajbakhsh , M. ; Lakouraj , M. M. ; Fadavi , A. Allyltriphenylphosphonium peroxodisulfate (CH2˭CHCH2PPh3)2S2O8: An efficient and convenient reagent for the oxidation of alcohols, silyl, and THP ethers under nonaqueous conditions . Synth. Commun. 2004 , 34 , 1173 – 1181 .
  • Tajbakhsh , M. ; Hosseinzadeh , R. ; Sadatshahabi , M. 2,6-Dicarboxypyridinium fluorochromate: A mild and efficient reagent for oxidative deprotection of trimethylsilyl ethers to their corresponding carbonyl compounds . Phosphorus, Sulfur Silicon Relat. Elem. 2005 , 180 , 2279 – 2283 .
  • 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 .
  • (a) Furniss , B. S. ; Manaford , A. J. ; Rogers , V. ; Smith , P. W. G. ; Tatchell , A. R. Vogel's Textbook of Practical Organic Chemistry, , 4th Ed. ; 1978 ; p. 1192 , 1196 ; (b) Shriner , R. L. ; Hermann , C. K. F. ; Morrill , T. C. ; Curtin , D. Y. ; Fuson , R. C. The Systematic Identification of Organic Compounds ; Wiley : New York , 2004 ; p. 652 .

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