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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 22
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Original Articles

Efficient Synthesis of meso-Tetraarylporphyrins Using I2 as Catalyst and IBX as Oxidant

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Pages 3990-3998 | Received 16 Oct 2008, Published online: 16 Oct 2009

REFERENCES

  • (a) Bartoli , J. F. ; Brigaud , O. ; Battioni , P. ; Mansuy , D. Hydroxylation of linear alkanes catalysed by iron porphyrins: Particular efficacy and regio selectivity of perhalogenated porphyrins . J. Chem. Soc., Chem. Commun. 1991 , 440 ; (b) Anelli , P. L. ; Banfi , S. ; Legramandi , F. ; Montanari , F. ; Pozzi , G. ; Quici , S. Tailed MnIII-tetraarylporphyrins bearing an axial ligand and/or a carboxylic group: Self-consistent catalysts for H2H2 or NaOCl alkene epoxidation . J. Chem. Soc., Perkin Trans. 1 1993 , 1345 – 1348 .
  • (a) Medforth , C. J. ; Berber , M. D. ; Smith , K. M. ; Shelnun , J. A. Tetracycloalkenyl-meso-tetraphenylporphyrins as models for the effect of non-planarity on the light absortion properties of photosynthetic chromophores . Tetrahedron Lett. 1990 , 31 , 3719 – 3722 ; (b) Migrom , L. R. Synthesis of some new tetra-arylporphyrins for studies in solar energy conversion . J. Chem Soc., Perkin Trans. 1 1983 , 2535 – 2539 .
  • (a) Driaf , K. ; Krauzz , P. ; Verneuil , B. ; Spiro , M. ; Blais , J. C. ; Bolbach , G. Glycosylated cationic porphyrins as potential agents in cancer phototherapy . Tetrahedron Lett. 1993 , 34 , 1027 – 1030 ; (b) Henderson , B. W. ; Dougherty , T. J. How does photodynamic therapy work? Photochem. Photobiol. 1992 , 55 , 145 – 147 .
  • Drain , C. M. ; Russell , K. C. ; Lehn , J. M. Synthesis, structure, and reactivity of ionogenic Sn(η-CpR)Cl derivatives . J. Chem. Soc., Chem. Commun. 1996 , 2337 – 2338 .
  • (a) Tabushi , I. Reductive dioxygen activation bu use of artifical P-450 system . Coord. Chem Rev. 1988 , 86 , 1 – 42 ; (b) Mori , T. ; Santa , T. ; Hirobe , M. Synthesis and cytochrome P-450-like reactivity of polypeptide-bound porphinatoiron(III) . Tetrahedron Lett. 1985 , 26 , 5555 – 5558 .
  • (a) Rothemund , P. Porphyrin studies, III: The structure of the porphine ring system . J. Am. Chem. Soc. 1939 , 61 , 2912 – 2915 ; (b) Rothemund , P. ; Menotti , A. R. Porphyrin studies, IV: The synthesis of α,β,γ,δ-tetraporphine . J. Am. Chem. Soc. 1941 , 63 , 267 – 270 .
  • (a) Adler , A. D. ; Longo , F. R. ; Finarelli , J. D. ; Goldmacher , J. ; Assour , J. ; Korsakoff , L. A simplified synthesis for meso-tetraphenylporphine . J. Org. Chem. 1967 , 32 , 476 – 476 ; (b) Kim , J. B. ; Leonard , J. J. ; Longo , F. R. Mechanistic study of the synthesis and spectral properties of meso-tetraarylporphyrins . J. Am. Chem. Soc. 1972 , 94 , 3986 – 3992 .
  • (a) Lindsey , J. S. ; Schreiman , I. C. ; Hsu , H. C. Rothemund and Adler–Longo reactions revisited: Synthesis of tetraphenylporphyrins under equilibrium conditions . J. Org. Chem. 1987 , 52 , 827 – 836 ; (b) Wagner , R. W. ; Johnson , T. E. ; Lindsey , J. S. Investigation of the one-flask synthesis of porphyrins bearing meso-linked straps of variable length, rigidity, and redox activity . Tetrahedron 1997 , 53 , 6755 – 6790 ; (c) Li , F. ; Yang , K. ; Tyhonas , J. S. ; MacCrum , K. A. ; Lindsey , J. S. Beneficial effects of salts on an acid-catalyzed condensation leading to porphyrin formation . Tetrahedron 1997 , 53 , 12339 – 12360 .
  • Geier , G. R. ; Ciringh , Y. ; Li , F. ; Haynes , D. M. ; Lindsey , J. S. A survey of acid catalysts for use in two-step, one-flask syntheses of meso-substituted porphyrinic macrocycles . Org. Lett. 2000 , 2 , 1745 – 1748 .
  • Onaka , M. ; Shinoda , T. ; Izumi , Y. ; Nolen , E. Clay-mediated meso-tetraarylporphyrin synthesis. Tetrahedron Lett. 1993, 34, 2625–2628.
  • Sharghi , H. ; Nejad , A. R. H. Synthesis of meso-tetraarylporphyrins in air with silica chloride as catalyst . J. Chem. Res. Synop. 2003 , 87 – 88 .
  • Kitaoka , S. ; Nobuoka , K. ; Ishikawa , Y. Ionic liquids for tetraarylporphyrin preparation . Tetrahedron 2005 , 61 , 7678 – 7685 .
  • Naik , R. ; Joshi , P. ; Kaiwar , S. P. ; Deshpande , R. K. Facile synthesis of meso-substituted dipyrromethanes and porphyrins using cation exchange resins . Tetrahedron 2003 , 59 , 2207 – 2213 .
  • (a) Hiroto , S. ; Osuka , A. meso-Alkyl-substituted meso–meso linked diporphyrins and meso-alkyl-substituted meso–meso, β–β, β–β triply linked diporphyrins . J. Org. Chem. 2005 , 70 , 4054 – 4058 ; (b) Hoshino , A. ; Ohgo , Y. ; Nakamura , M. Synthesis and inversion barriers of undeca- and dodeca-substituted saddle shaped porphyrin complexes . Tetrahedron Lett. 2005 , 46 , 4961 – 4964 .
  • (a) Hartman , C. ; Meyer , V. Ueber jodobenzoesaure . Chem. Ber. 1893 , 26 , 1727 – 1732 ; (b) Dess , D. B. ; Martin , J. C. Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones . J. Org. Chem. 1983 , 48 , 4155 – 4165 ; (c) Dess , B. D. ; Martin , J. C. A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary acohols and a variety of related 12-I-5 species . J. Am. Chem. Soc. 1991 , 113 , 7277 – 7278 .
  • (a) Frigerio , M. ; Santagostino , M. A mild oxidizing reagent for alcohols and 1,2-diols: o-Iodoxybenzoic acid (IBX) in DMSO . Tetrahedron Lett. 1994 , 35 , 8019 – 8022 ; (b) Frigerio , M. ; Santagostino , M. ; Sputore , S. ; Palmisano , G. Oxidation of alcohols with o-iodoxybenzoic acid in DMSO: A new insight into an old hypervalent iodine reagent . J. Org. Chem. 1995 , 60 , 7272 – 7276 ; (c) De Munari , S. ; Frigerio , M. ; Santagostino , M. Hypervalent iodine oxidants: Structure and kinetics of the reactive intermediates in the oxidation of alcohols and 1,2-diols by o-iodoxybenzoic acid (IBX) and Dess–Martin periodinane: A comparative 1H-NMR study . J. Org. Chem. 1996 , 61 , 9272 – 9279 .
  • Duan , L. ; Wang , Y. L. ; Fan , X. S. ; Wang , J. Y. Novel synthesis of meso-tetraarylporphyrins by using I2 as catalyst and air as oxidant under thermal or UV conditions . Chem. Lett. 2008 , 37 , 112 – 113 .
  • (a) Lindsey , J. S. ; MacCrum , K. A. ; Tyhonas , J. S. ; Chuang , Y. Y. Investigation of a synthesis of meso-porphyrins employing high concentration conditions and an electron transport chain for aerobic oxidation . J. Org. Chem. 1994 , 59 , 579 – 587 ; (b) Shoji , O. ; Okada , S. ; Satake , A. ; Kobuke , Y. Coordination assembled rings of ferrocene-bridged trisporphyrin with flexible hinge-like motion: Selective dimer ring formation, its transformation to larger rings, and vice versa . J. Am. Chem. Soc. 2005 , 127 , 2201 .

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