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Volumn 39, Issue 22, 2009, Pages 3990-3998

Efficient synthesis of meso-tetraarylporphyrins using i2 as catalyst and ibx as oxidant

Author keywords

Aldehydes; IBX; Meso tetraarylporphyrins; Pyrrole; Synthesis

Indexed keywords

5,10,15,20 TETRAKIS(2 BROMOPHENYL)PORPHYRIN; 5,10,15,20 TETRAKIS(2 CHLOROPHENYL)PORPHYRIN; 5,10,15,20 TETRAKIS(2 FLUOROPHENYL)PORPHYRIN; 5,10,15,20 TETRAKIS(2 METHOXYPHENYL)PORPHYRI; 5,10,15,20 TETRAKIS(2 METHYLPHENYL)PORPHYRIN; 5,10,15,20 TETRAKIS(3 BROMOPHENYL)PORPHYRIN; 5,10,15,20 TETRAKIS(3 CHLOROPHENYL)PORPHYRIN; 5,10,15,20 TETRAKIS(3 METHOXYPHENYL)PORPHYRIN; 5,10,15,20 TETRAKIS(4 METHOXYPHENYL)PORPHYRIN; 5,10,15,20 TETRAKIS(4 METHYLPHENYL)PORPHYRIN; 5,10,15,20 TETRAKIS(4 NITROPHENYL)PORPHYRIN; 5,10,15,20 TETRAPHENYLPORPHYRIN; BENZOIC ACID DERIVATIVE; IODINE; IODOXYBENZOIC ACID; MESO TETRAARYLPORPHYRIN DERIVATIVE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 70350637379     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902883595     Document Type: Article
Times cited : (10)

References (32)
  • 1
    • 0025975268 scopus 로고
    • Hydroxylation of linear alkanes catalysed by iron porphyrins: Particular efficacy and regio selectivity of perhalogenated porphyrins
    • 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
    • (1991) J. Chem. Soc., Chem. Commun. , vol.440
    • Bartoli, J.F.1    Brigaud, O.2    Battioni, P.3    Mansuy, D.4
  • 3
    • 0025358916 scopus 로고
    • Tetracy-cloalkenyl-meso-tetraphenylporphyrins as models for the effect of non-planarity on the light absortion properties of photosynthetic chromo-phores.
    • Medforth, C. J.; Berber, M. D.; Smith, K. M.; Shelnun, J. A. Tetracy-cloalkenyl-meso-tetraphenylporphyrins as models for the effect of non-planarity on the light absortion properties of photosynthetic chromo-phores. Tetrahedron Lett. 1990, 31, 3719-3722
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3719-3722
    • Medforth, C.J.1    Berber, M.D.2    Smith, K.M.3    Shelnun, J.A.4
  • 4
    • 37049099069 scopus 로고
    • Synthesis of some new tetra-arylporphyrins for studies in solar energy conversion
    • Migrom L. R. Synthesis of some new tetra-arylporphyrins for studies in solar energy conversion. J. Chem Soc. Perkin Trans. 1, 1983: 2535-2539.
    • (1983) J. Chem Soc. Perkin Trans. , vol.1 , pp. 2535-2539
    • Migrom, L.R.1
  • 5
  • 6
    • 0026494593 scopus 로고
    • How does photodynamic therapy work? Photochem.
    • Henderson, B. W.; Dougherty, T. J. How does photodynamic therapy work? Photochem. Photobiol. 1992, 55, 145-147.
    • (1992) Photobiol. , vol.55 , pp. 145-147
    • Henderson, B.W.1    Dougherty, T.J.2
  • 8
    • 0042920807 scopus 로고
    • Reductive dioxygen activation bu use of artifical P-450 system
    • Tabushi, I. Reductive dioxygen activation bu use of artifical P-450 system. Coord. Chem Rev. 1988, 86, 1-42
    • (1988) Coord. Chem Rev. , vol.86 , pp. 1-42
    • Tabushi, I.1
  • 9
    • 0001084554 scopus 로고
    • Synthesis and cytochrome P-450-like reactivity of polypeptide-bound porphinatoir-on(III).
    • Mori, T.; Santa, T.; Hirobe, M. Synthesis and cytochrome P-450-like reactivity of polypeptide-bound porphinatoir-on(III). Tetrahedron Lett. 1985, 26, 5555-5558.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5555-5558
    • Mori, T.1    Santa, T.2    Hirobe, M.3
  • 10
    • 33947438220 scopus 로고
    • Porphyrin studies, III: The structure of the porphine ring system
    • Rothemund, P. Porphyrin studies, III: The structure of the porphine ring system. J. Am. Chem. Soc. 1939, 61, 2912-2915
    • (1939) J. Am. Chem. Soc. , vol.61 , pp. 2912-2915
    • Rothemund, P.1
  • 11
    • 0001055374 scopus 로고
    • Porphyrin studies, IV: The synthesis of a,b,c,d-tetraporphine
    • Rothemund, P.; Menotti, A. R. Porphyrin studies, IV: The synthesis of a,b,c,d-tetraporphine. J. Am. Chem. Soc. 1941, 63, 267-270.
    • (1941) J. Am. Chem. Soc. , vol.63 , pp. 267-270
    • Rothemund, P.1    Menotti, A.R.2
  • 13
    • 0015530789 scopus 로고
    • Mechanistic study of the synthesis and spectral properties of meso-tetraarylporphyrins
    • 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.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 3986-3992
    • Kim, J.B.1    Leonard, J.J.2    Longo, F.R.3
  • 14
    • 0006368032 scopus 로고
    • Rothemund and Adler-Longo reactions revisited: Synthesis of tetraphenylporphyrins under equilibrium conditions
    • 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
    • (1987) J. Org. Chem. , vol.52 , pp. 827-836
    • Lindsey, J.S.1    Schreiman, I.C.2    Hsu, H.C.3
  • 15
    • 0031009823 scopus 로고    scopus 로고
    • Investigation of the one-flask synthesis of porphyrins bearing meso-linked straps of variable length, rigidity, and redox activity.
    • 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
    • (1997) Tetrahedron , vol.53 , pp. 6755-6790
    • Wagner, R.W.1    Johnson, T.E.2    Lindsey, J.S.3
  • 16
    • 0030768671 scopus 로고    scopus 로고
    • Beneficial effects of salts on an acid-catalyzed condensation leading to porphyrin formation.
    • 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.
    • (1997) Tetrahedron , vol.53 , pp. 12339-12360
    • Li, F.1    Yang, K.2    Tyhonas, J.S.3    MacCrum, K.A.4    Lindsey, J.S.5
  • 17
    • 0034658882 scopus 로고    scopus 로고
    • A survey of acid catalysts for use in two-step, one-flask syntheses of meso-substituted porphyrinic macrocycles
    • 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.
    • (2000) Org. Lett. , vol.2 , pp. 1745-1748
    • Geier, G.R.1    Ciringh, Y.2    Li, F.3    Haynes, D.M.4    Lindsey, J.S.5
  • 18
    • 0027536859 scopus 로고
    • Clay-mediated meso-tetraaryl-porphyrin synthesis.
    • Onaka, M.; Shinoda, T.; Izumi, Y.; Nolen, E. Clay-mediated meso-tetraaryl-porphyrin synthesis. Tetrahedron Lett. 1993, 34, 2625-2628.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2625-2628
    • Onaka, M.1    Shinoda, T.2    Izumi, Y.3    Nolen, E.4
  • 19
    • 0037628947 scopus 로고    scopus 로고
    • Synthesis of meso-tetraarylporphyrins in air with silica chloride as catalyst
    • Sharghi, H.; Nejad, A. R. H. Synthesis of meso-tetraarylporphyrins in air with silica chloride as catalyst. J. Chem. Res. Synop. 2003, 87-88.
    • (2003) J. Chem. Res. Synop. , pp. 87-88
    • Sharghi, H.1    Nejad, A.R.H.2
  • 20
    • 21844444571 scopus 로고    scopus 로고
    • Ionic liquids for tetraarylporphyrin preparation.
    • Kitaoka, S.; Nobuoka, K.; Ishikawa, Y. Ionic liquids for tetraarylporphyrin preparation. Tetrahedron 2005, 61, 7678-7685.
    • (2005) Tetrahedron , vol.61 , pp. 7678-7685
    • Kitaoka, S.1    Nobuoka, K.2    Ishikawa, Y.3
  • 21
    • 0037463771 scopus 로고    scopus 로고
    • Facile synthesis of meso-substituted dipyrromethanes and porphyrins using cation exchange resins.
    • 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.
    • (2003) Tetrahedron , vol.59 , pp. 2207-2213
    • Naik, R.1    Joshi, P.2    Kaiwar, S.P.3    Deshpande, R.K.4
  • 22
    • 18744408478 scopus 로고    scopus 로고
    • Meso-Alkyl-substituted meso-meso linked diporphyrins and meso-alkyl-substituted meso-meso, b-b, b-b triply linked diporphyrins
    • Hiroto, S.; Osuka, A. meso-Alkyl-substituted meso-meso linked diporphyrins and meso-alkyl-substituted meso-meso, b-b, b-b triply linked diporphyrins. J. Org. Chem. 2005, 70, 4054-4058
    • (2005) J. Org. Chem. , vol.70 , pp. 4054-4058
    • Hiroto, S.1    Osuka, A.2
  • 23
    • 20544437655 scopus 로고    scopus 로고
    • Synthesis and inversion barriers of undeca-and dodeca-substituted saddle shaped porphyrin complexes.
    • 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.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 4961-4964
    • Hoshino, A.1    Ohgo, Y.2    Nakamura, M.3
  • 24
    • 56249137056 scopus 로고
    • Ueber jodobenzoesaure
    • Hartman, C.; Meyer, V. Ueber jodobenzoesaure. Chem. Ber. 1893, 26, 1727-1732
    • (1893) Chem. Ber. , vol.26 , pp. 1727-1732
    • Hartman, C.1    Meyer, V.2
  • 25
    • 33644528891 scopus 로고
    • Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
    • 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
    • (1983) J. Org. Chem. , vol.48 , pp. 4155-4165
    • Dess, D.B.1    Martin, J.C.2
  • 26
    • 3042741556 scopus 로고
    • 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
    • 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.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7277-7278
    • Dess, B.D.1    Martin, J.C.2
  • 27
    • 0027988788 scopus 로고
    • A mild oxidizing reagent for alcohols and 1,2-diols: O-Iodoxybenzoic acid (IBX) in DMSO.
    • 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
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8019-8022
    • Frigerio, M.1    Santagostino, M.2
  • 28
    • 0000295212 scopus 로고
    • Oxidation of alcohols with o-iodoxybenzoic acid in DMSO: A new insight into an old hypervalent iodine reagent
    • 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
    • (1995) J. Org. Chem. , vol.60 , pp. 7272-7276
    • Frigerio, M.1    Santagostino, M.2    Sputore, S.3    Palmisano, G.4
  • 29
    • 0000565339 scopus 로고    scopus 로고
    • 1H-NMR study
    • 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.
    • (1996) J. Org. Chem. , vol.61 , pp. 9272-9279
    • De Munari, S.1    Frigerio, M.2    Santagostino, M.3
  • 30
    • 38949193893 scopus 로고    scopus 로고
    • 2 as catalyst and air as oxidant under thermal or UV conditions
    • 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.
    • (2008) Chem. Lett. , vol.37 , pp. 112-113
    • Duan, L.1    Wang, Y.L.2    Fan, X.S.3    Wang, J.Y.4
  • 31
    • 0001968112 scopus 로고
    • Investigation of a synthesis of meso-porphyrins employing high concentration conditions and an electron transport chain for aerobic oxidation
    • 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
    • (1994) J. Org. Chem. , vol.59 , pp. 579-587
    • Lindsey, J.S.1    MacCrum, K.A.2    Tyhonas, J.S.3    Chuang, Y.Y.4
  • 32
    • 13944272205 scopus 로고    scopus 로고
    • Coordination assembled rings of ferrocene-bridged trisporphyrin with flexible hinge-like motion: Selective dimer ring formation, its transformation to larger rings, and vice versa
    • 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.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 2201
    • Shoji, O.1    Okada, S.2    Satake, A.3    Kobuke, Y.4


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