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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 17
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Original Articles

One-Pot Protocol for Synthesis of α-Organosulfonyloxy Ketones from Secondary Alcohols Using Hypervalent Iodine(V)–Mediated Oxidations

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Pages 3101-3110 | Received 08 Nov 2008, Published online: 03 Aug 2009

REFERENCES

  • (a) Tuncay , A. ; Dustman , J. A. ; Fisher , G. ; Tuncay , C. I. Ultrasound-promoted hypervalent iodine reactions: (α-Tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene . Tetrahedron Lett. 1992 , 33 , 7647 ; (b) Moriarty , R. M. ; Vaid , B. K. ; Duncan , M. P. ; Levy , S. G. ; Prakash , O. ; Goyal , S. A one-pot synthesis of 2-amino- and 2-(arylamino)-substituted thiazoles and selenazoles using [hydroxy(tosyloxy)iodo]benzene, carbonyl compounds, and thioureas or selenoureas: A modification of the Hantzsch synthesis . Synthesis 1992 , 845 ; (c) Prakash , O. ; Goyal , S. A new synthesis of 2-aroylcoumaran-3-ones by hypervalent iodine oxidation of 2-acetyl-phenyl benzoates using [hydroxy(tosyloxy)iodo]benzene . Synthesis 1992 , 629 .
  • (a) Prakash , O. ; Saini , N. ; Sharma , P. K. Hypervalent iodine reagents in the synthesis of heterocyclic compounds . Synlett 1994 , 221 ; (b) Varma , R. S. ; Kumar , D. ; Liesen , P. J. Solid state synthesis of 2-aroylbenzo[b]furans, 1,3-thiazoles, and 3-aryl-5,6-dihydroimidazo[2,1-b][1,3]thiazoles from α-tosyloxyketones using microwave irradiation . J. Chem. Soc., Perkin Trans. 1 1998 , 4093 ; (c) Koser , G. F. Oxysulfonylation of carbonyl compounds at the α-carbon . Aldrichim. Acta 2001 , 34 , 89 ; (d) Nicolaou , K. C. ; Mantagnon , T. ; Ulven , T. ; Baran , P. S. ; Zhong , Y. L. ; Sarabia , F. Novel chemistry of α-tosyloxy ketones: Applications to the solution- and solid-phase synthesis of privileged heterocycle and enediyne libraries . J. Am. Chem. Soc. 2002 , 124 , 5718 .
  • (a) Lodaya , J. S. ; Koser , G. F. Direct α-mesyloxylation of ketones and β-dicarbonyl compounds with [hydroxy(mesyloxy)iodo]benzene . J. Org. Chem. 1988 , 53 , 210 ; (b) Prakash , O. ; Pannu , K. ; Prakash , R. ; Batra , A. [Hydroxy(tosyloxy)iodo]benzene-mediated α-azidation of ketones . Molecules 2006 , 11 , 523 ; (c) Prakash , O. ; Rani , N. ; Goyal , S. Hypervalent iodine in the synthesis of bridgehead heterocycles: Novel and facile syntheses of 3-substituted-5,6-dihydroimidazo[2,1-b]thiazoles and 3-phenylthiazolo[3,2-a]benzimidazole from acetophenones using [hydroxy(tosyloxy)iodo]benzene . J. Chem. Soc., Perkin Trans. 1 1992 , 707 .
  • (a) Ladziata , U. ; Zhadankin , V. V. Hypervalent iodine oxidation of 1-phenyl-3-arylpyrazole-4-carboxaldehyde oximes: A facile and efficient synthesis of new 3,4-bis(1-phenyl-3-arylpyrazolyl)-1,2,5-oxadiazole-N-oxides . Arkivoc 2006 , 9 , 26 ; (b) Zhadankin , V. V. ; Stang , P. Recent developments in the chemistry of polyvalent iodine compounds . Chem. Rev. 2002 , 102 , 2523 ; (c) Zhadankin , V. V. Benziodoxole-based hypervalent iodine reagents in organic synthesis . Curr. Org. Synth. 2005 , 2 , 221 ; (c) Fontaine , P. ; Chiaroni , A. ; Masson , G. ; Zhu , J. One-pot three-component synthesis of α-iminonitriles by IBX/TBAB-mediated oxidative Strecker reaction . Org. Lett. 2008 , 10 , 1509 .
  • Mahajan , U. S. ; Akamanchi , K. G. A new application of hypervalent iodine (λ 5) reagents with organosulfonic acids for direct α-organosulfonyloxylation carbonyl compounds . Synlett 2008 , 987 .
  • Trost , B. M. Comprehensive Organic Chemistry ; I. Fleming (Ed.) ; Pergamon : Oxford , 1971 ; vol. 7 , p. 251 ; (b) Larock , R. C. Comprehensive Organic Transformation ; Wiley-VCH : New York , 1999 , p. 1234 .
  • (a) Khanna , M. S. ; Garg , C. P. ; Kapoor , R. P. α-Tosyloxylation of enolizable ketones using thallium(III) p-tolylsulphonate (TTS) . Tetrahedron Lett. 1992 , 33 , 1495 ; (b) Oliver , R. S. J. ; Killeen , N. M. ; Knowles , D. A. ; Yau , S. C. ; Bagley , M. C. ; Tomkinson , Nicholas, C. O. Direct α-oxytosylation of carbonyl compounds: One-pot synthesis of heterocycles . Org. Lett. 2007 , 9 , 4009 ; (c) Creary , X. ; Rollin , A. J. Reaction of α-keto triflates with sodium methoxide . J. Org. Chem. 1977 , 42 , 4226 ; (d) Charrlon , J. L. ; Lai , H. K. ; Lypka , G. N. Photoreactions of α-sulfonyloxyketones . Can. J. Chem. 1980 , 58 , 458 .
  • (a) Nabana , T. ; Togo , H. Reactivities of novel [hydroxy(tosyloxy)iodo]arenes and [hydroxy(phosphoryloxy)iodo]arenes for α-tosyloxylation and α-phosphoryloxylation of ketones . J. Org. Chem. 2002 , 67 , 4362 ; (b) Makoto , U. ; Takahiro , N. ; Togo , H. Novel oxidative α-tosyloxylation of alcohols with iodosylbenzene and p-toluenesulfonic acid and its synthetic use for direct preparation of heteroaromatics . J. Org. Chem. 2003 , 68 , 6424 ; (c) Lodaya , J. S. ; Koser , G. F. Direct α-mesyloxylation of ketones and β-dicarbonyl compounds with [hydroxy(mesyloxy)iodo]benzene . J. Org. Chem. 1988 , 53 , 210 .
  • (a) Yusubov , M. S. ; Wirth , T. Solvent-free reactions with hypervalent iodine reagents . Org. Lett. 2005 , 7 , 519 ; (b) Toda , F. ; Tanaka , K. ; Sekikawa , A. Host–guest complex formation by a solid–solid reaction . J. Chem. Soc., Chem. Commun. 1987 , 279 .

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