Skip to main content

Functionalization of Corroles

  • Chapter
  • First Online:
Synthesis and Modifications of Porphyrinoids

Abstract

Corroles have assumed an important place in tetrapyrrolic chemistry. This review highlights the reactivity features of meso-arylcorroles under different reaction conditions.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Johnson AW, Price R (1960) Synthesis of derivatives of corrole (pentahydrocorrin). J Chem Soc 1649

    Google Scholar 

  2. Johnson AW, Kay IT (1965) Corroles. Part I. Synthesis. J Chem Soc 1620

    Google Scholar 

  3. Gross Z, Galili N, Saltsman I (1999) The first direct synthesis of corroles from pyrrole. Angew Chem Int Ed 38:1427

    CAS  Google Scholar 

  4. Paolesse R, Jaquinod L, Nurco DJ, Mini S, Sagone F, Boschi T, Smith KM (1999) 5,10,15-Triphenylcorrole: a product from a modified Rothemund reaction. Chem Commun 1307

    Google Scholar 

  5. Gryko DT, Koszarna B (2003) Refined methods for the synthesis of meso-substituted A3- and trans-A2B-corroles. Org Biomol Chem 1:350

    CAS  Google Scholar 

  6. Lindsey JS (2000) Synthesis of meso-substituted porphyrins. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook. Academic, Boston

    Google Scholar 

  7. Koszarna B, Gryko DT (2006) Efficient synthesis of meso-substituted corroles in a H2O-MeOH mixture. J Org Chem 71:3707

    CAS  Google Scholar 

  8. Collman JP, Decréau RA (2003) Microwave-assisted synthesis of corroles. Tetrahedron Lett 44:1207–1210

    CAS  Google Scholar 

  9. Kumari P, Chauhan SMS (2008) Efficient synthesis of 5,10,15-triarylcorroles using Amberlyst 15 under solvent-free conditions. J Heterocycl Chem 45:779

    CAS  Google Scholar 

  10. Zhan HY, Liu HY, Chen HJ, Jiang HF (2009) Preparation of meso-substituted trans-A2B-corroles in ionic liquids. Tetrahedron Lett 50:2196

    CAS  Google Scholar 

  11. Dogutan DK, Stoian SA, McGuire R, Schwalbe M, Teets TS, Nocera DG (2011) Hangman corroles: efficient synthesis and oxygen reaction chemistry. J Am Chem Soc 133:131

    CAS  Google Scholar 

  12. Nardis S, Monti D, Paolesse R (2005) Novel aspects of corrole chemistry. Mini Rev Org Chem 2:355

    CAS  Google Scholar 

  13. Schwalbe M, Dogutan DK, Stoian SA, Teets TS, Nocera DG (2011) Xanthene-modified and Hangman iron corroles. Inorg Chem 50:1368

    CAS  Google Scholar 

  14. Tasior M, Gryko DT, Pielachinska DJ, Zanelli A, Flamigni L (2010) Trans-A2B-corroles bearing a Coumarin moiety – from synthesis to photophysics. Chem Asian J 5:130

    CAS  Google Scholar 

  15. Flamigni L, Wyrostek D, Voloshchuk R, Gryko DT (2010) Solvent polarity effect on intramolecular electron transfer in a corrole-naphthalene bisimide dyad. Phys Chem Chem Phys 12:474

    CAS  Google Scholar 

  16. Paolesse R (2008) Corrole: the little big porphyrinoid. Synlett 15:2215

    Google Scholar 

  17. Gryko DT (2008) Adventures in the synthesis of meso-substituted corroles. J Porphyrins Phthalocyanines 12:906

    CAS  Google Scholar 

  18. Bröring M, Milsmann C, Ruck S, Köhler S (2009) Bis-picket-fence corroles. J Organomet Chem 694:1011

    Google Scholar 

  19. El Ojaimi M, Gros CP, Barbe J-M (2008) Efficient two-step synthesis of face-to-face meso-substituted bis(corrole) dyads. Eur J Org Chem 1181

    Google Scholar 

  20. Rohand T, Dolusic E, Ngo TH, Maes W, Dehaen W (2007) Efficient synthesis of aryldipyrromethanes in water and their application in the synthesis of corroles and dipyrromethenes. Arkivoc: 307

    Google Scholar 

  21. Guilard R, Gryko DT, Canard G, Barbe J-M, Koszarna B, Brandes S, Tasior M (2002) Synthesis of corroles bearing up to three different meso substituents. Org Lett 4:4491

    CAS  Google Scholar 

  22. Gryko DT, Jadach K (2001) A simple and versatile one-pot synthesis of meso-substituted trans-A2B-corroles. J Org Chem 66:4267

    CAS  Google Scholar 

  23. Aviv-Harel I, Gross Z (2009) Aura of corroles. Chem Eur J 15:8382

    CAS  Google Scholar 

  24. Flamigni L, Gryko DT (2009) Photoactive corrole-based arrays. Chem Soc Rev 38:1635

    CAS  Google Scholar 

  25. Aviv I, Gross Z (2007) Corrole-based applications. Chem Commun 1987

    Google Scholar 

  26. Aviv-Harel I, Gross Z (2011) Coordination chemistry of corroles with focus on main group elements. Coord Chem Rev 255:717

    CAS  Google Scholar 

  27. Harvey PD, Stern C, Gros CP, Guilard R (2007) The photophysics and photochemistry of cofacial free base and metallated bisporphyrins held together by covalent architectures. Coord Chem Rev 251:401

    CAS  Google Scholar 

  28. Palmer JH (2012) Transitions metals corroles coordination chemistry. In: Mingos DMP, Day P, Dahl JP (eds) Molecular electronic structures of transition metal complexes I. Springer, Heidelberg

    Google Scholar 

  29. Paolesse R, Nardis S, Venanzi M, Mastroianni M, Russo M, Fronczek FR, Vicente MGH (2003) Vilsmeier formylation of 5,10,15-triphenylcorrole: expected and unusual products. Chem Eur J 9:1192

    CAS  Google Scholar 

  30. Saltsman I, Goldberg I, Gross Z (2003) One-step conversions of a simple corrole into chiral and amphiphilic derivatives. Tetrahedron Lett 44:5669

    CAS  Google Scholar 

  31. Gross Z, Galili N (1999) N-Substituted corroles: a novel class of chiral ligands. Angew Chem Int Ed 38:2366

    CAS  Google Scholar 

  32. Simkhovich L, Mahammed A, Goldberg I, Gross Z (2001) Synthesis and characterization of germanium, tin, phosphorus, iron, and rhodium complexes of tris(pentafluorophenyl)corrole, and the utilization of the iron and rhodium corroles as cyclopropanation catalysts. Chem Eur J 7:1041

    CAS  Google Scholar 

  33. Simkhovich L, Iyer P, Goldberg I, Gross Z (2002) Structure and chemistry of N-substituted corroles and their rhodium(I) and zinc(II) metal-ion complexes. Chem Eur J 8:2595

    CAS  Google Scholar 

  34. Tardieux C, Gros CP, Guilard R (1998) On corrole chemistry. An isomerization study and oxidative cleavage of the corrole macroring to a biliverdin structure. J Heterocycl Chem 35:965

    CAS  Google Scholar 

  35. Paolesse R, Sagone F, Macagnano A, Boschi T, Prodi L, Montalti M, Zaccheroni N, Bolletta F, Smith KM (1999) Photophysical behaviour of corrole and its symmetrical and unsymmetrical dyads. J Porphyrins Phthalocyanines 3:364

    CAS  Google Scholar 

  36. Gros CP, Barbe JM, Espinosa E, Guilard R (2006) Room-temperature autoconversion of free-base corrole into free-base porphyrin. Angew Chem Int Ed 45:564

    Google Scholar 

  37. Swider P, Nowak-Krol A, Voloshchuk R, Lewtak JP, Gryko DT, Danikiewicz W (2010) Mass spectrometry studies on meso-substituted corroles and their photochemical decomposition products. J Mass Spectrom 45:1443

    CAS  Google Scholar 

  38. Barata JFB, Neves MGPMS, Tomé AC, Faustino MAF, Silva AMS, Cavaleiro JAS (2010) How light affects 5,10,15-tris(pentafluorophenyl)corrole. Tetrahedron Lett 51:1537

    CAS  Google Scholar 

  39. Hirabayashi S, Omote M, Aratani N, Osuka A (2012) Directly linked corrole oligomers via facile oxidative3–3 coupling reaction. Bull Chem Soc Jpn 85:558

    CAS  Google Scholar 

  40. Stefanelli M, Shen J, Zhu WH, Mastroianni M, Mandoj F, Nardis S, Ou ZP, Kadish KM, Fronczek FR, Smith KM, Paolesse R (2009) Demetalation of silver(III) corrolates. Inorg Chem 48:6879

    CAS  Google Scholar 

  41. Manoj F, Nardis S, Pomarico G, Paolesse R (2008) Demetalation of corrole complexes: an old dream turning into reality. J Porphyrins Phthalocyanines 12:19

    Google Scholar 

  42. Ngo TH, Van Rossom W, Dehaen W, Maes W (2009) Reductive demetallation of Cu-corroles – a new protective strategy towards functional free-base corroles. Org Biomol Chem 7:439

    CAS  Google Scholar 

  43. Paolesse R, Nardis S, Sagone F, Khoury RG (2001) Synthesis and functionalization of meso-aryl-substituted corroles. J Org Chem 66:550

    CAS  Google Scholar 

  44. Du R-B, Liu C, Shen D-M, Chen Q-Y (2009) Partial bromination and fluoroalkylation of 5,10,15-tris(pentafluorophenyl)corrole. Synlett 16:2701

    Google Scholar 

  45. Nardis S, Pomarico G, Mandoj F, Fronczek FR, Smith KM, Paolesse R (2010) One-pot synthesis of meso-alkyl substituted isocorroles: the reaction of a triarylcorrole with Grignard reagent. J Porphyrins Phthalocyanines 14:752

    CAS  Google Scholar 

  46. Nardis S, Mandoj F, Paolesse R, Fronczek FR, Smith KM, Prodi L, Montalti M, Battistini G (2007) Synthesis and functionalization of germanium triphenylcorrolate: the first example of a partially brominated corrole. Eur J Inorg Chem 2345

    Google Scholar 

  47. Palmer JH, Durrell AC, Gross Z, Winkler JR, Gray HB (2010) Near-IR phosphorescence of iridium(III) corroles at ambient temperature. J Am Chem Soc 132:9230

    CAS  Google Scholar 

  48. Wagnert L, Rubin R, Berg A, Mahammed A, Gross Z, Levanon H (2010) Photoexcited triplet state properties of brominated and nonbrominated Ga(III)-corroles as studied by time-resolved electron paramagnetic resonance. J Phys Chem B 114:14303

    CAS  Google Scholar 

  49. Wagnert L, Berg A, Stavitski E, Berthold T, Kothe G, Goldberg I, Mahammed A, Simkhovich L, Gross Z, Levanon H (2006) Exploring the photoexcited triplet states of aluminum and tin corroles by time-resolved Q-band EPR. Appl Magn Reson 30:591

    CAS  Google Scholar 

  50. Palmer JH, Day MW, Wilson AD, Henling LM, Gross Z, Gray HB (2008) Iridium corroles. J Am Chem Soc 130:7786

    CAS  Google Scholar 

  51. Mahammed A, Tumanskii B, Gross Z (2011) Effect of bromination on the electrochemistry, frontier orbitals and spectroscopy of metallocorroles. J Porphyrins Phthalocyanines 15:1275

    CAS  Google Scholar 

  52. Wasbotten IH, Wondimagegn T, Ghosh A (2002) Electronic absorption, resonance Raman, and electrochemical studies of planar and saddled copper(III) meso-triarylcorroles. Highly substituent-sensitive Soret bands as a distinctive feature of high-valent transition metal corroles. J Am Chem Soc 124:8104

    CAS  Google Scholar 

  53. Golubkov G, Bendix J, Gray HB, Mahammed A, Goldberg I, DiBilio AJ, Gross Z (2001) High-valent manganese corroles and the first perhalogenated metallocorrole catalyst. Angew Chem Int Ed 40:2132

    CAS  Google Scholar 

  54. Schechter A, Stanevsky M, Mahammed A, Gross Z (2012) Four-electron oxygen reduction by brominated cobalt corrole. Inorg Chem 51:22

    CAS  Google Scholar 

  55. Mahammed A, Gray HB, Meier-Callahan AE, Gross Z (2003) Aerobic oxidations catalyzed by chromium corroles. J Am Chem Soc 125:1162

    CAS  Google Scholar 

  56. Ngo TH, Puntoriero F, Nastasi F, Robeyns K, Van Meervelt L, Campagna S, Dehaen W, Maes W (2010) Synthetic, structural, and photophysical exploration of meso-pyrimidinyl-substituted AB2-corroles. Chem Eur J 16:5691

    CAS  Google Scholar 

  57. Mahammed A, Botoshansky M, Gross Z (2012) Chlorinated corroles. Dalton Trans 41:10938

    CAS  Google Scholar 

  58. Vestfrid J, Botoshansky M, Palmer JH, Durrell AC, Gray HB, Gross Z (2011) Iodinated aluminum(III) corroles with long-lived triplet excited states. J Am Chem Soc 133:12899

    CAS  Google Scholar 

  59. Mahammed A, Goldberg I, Gross Z (2001) Highly selective chlorosulfonation of tris(pentafluorophenyl)corrole as a synthetic tool for the preparation of amphiphilic corroles and metal complexes of planar chirality. Org Lett 3:3443

    CAS  Google Scholar 

  60. Mahammed A, Gross Z (2010) Chlorosulfonated corrole: a versatile synthon for advanced materials. J Porphyrins Phthalocyanines 14:911

    CAS  Google Scholar 

  61. Gross Z, Mahammed A (2002) Selective sulfonation and deuteration of free-base corroles. J Porphyrins Phthalocyanines 6:553

    CAS  Google Scholar 

  62. Saltsman I, Mahammed A, Goldberg I, Tkachenko E, Botoshansky M, Gross Z (2002) Selective substitution of corroles: nitration, hydroformylation, and chlorosulfonation. J Am Chem Soc 124:7411

    CAS  Google Scholar 

  63. Agadjanian H, Weaver JJ, Mahammed A, Rentsendorj A, Bass S, Kim J, Dmochowski IJ, Margalit R, Gray HB, Gross Z, Medina-Kauwe LK (2006) Specific delivery of corroles to cells via noncovalent conjugates with viral proteins. Pharm Res 23:367

    CAS  Google Scholar 

  64. Lim P, Mahammed A, Okun Z, Saltsman I, Gross Z, Gray HB, Termini J (2012) Differential cytostatic and cytotoxic action of metallocorroles against human cancer cells: potential platforms for anticancer drug development. Chem Res Toxicol 25:400

    CAS  Google Scholar 

  65. Hwang JY, Lubow DJ, Sims JD, Gray HB, Mahammed A, Gross Z, Medina-Kauwe LK, Farkas DL (2012) Investigating photoexcitation-induced mitochondrial damage by chemotherapeutic corroles using multimode optical imaging. J Biomed Opt 17:015003-1

    Google Scholar 

  66. Agadjanian H, Ma J, Rentsendorj A, Valluripalli V, Hwang JY, Mahammed A, Farkas DL, Gray HB, Gross Z, Medina-Kauwe LK (2009) Tumor detection and elimination by a targeted gallium corrole. Proc Natl Acad Sci USA 106:6105

    CAS  Google Scholar 

  67. Haber A, Aviram M, Gross Z (2012) Variables that influence cellular uptake and cytotoxic/cytoprotective effects of macrocyclic iron complexes. Inorg Chem 51:28

    CAS  Google Scholar 

  68. Catrinescu M-M, Chan W, Mahammed A, Gross Z, Levin LA (2012) Superoxide signaling and cell death in retinal ganglion cell axotomy: effects of metallocorroles. Exp Eye Res 97:31

    CAS  Google Scholar 

  69. Hwang JY, Lubow J, Chu D, Ma J, Agadjanian H, Sims J, Gray HB, Gross Z, Farkas DL, Medina-Kauwe LK (2011) A mechanistic study of tumor-targeted corrole toxicity. Mol Pharm 8:2233

    CAS  Google Scholar 

  70. Hwang JY, Lubow J, Chu D, Sims J, Alonso-Valenteen F, Gray HB, Gross Z, Farkas DL, Medina-Kauwe LK (2012) Photoexcitation of tumor-targeted corroles induces singlet oxygen-mediated augmentation of cytotoxicity. J Control Release 163:368

    CAS  Google Scholar 

  71. Sudhakar K, Velkannan V, Giribabu L (2012) Synthesis, electrochemical and photophysical properties of β-carboxy triarylcorroles. Tetrahedron Lett 53:991

    CAS  Google Scholar 

  72. Vale LSHP, Barata JFB, Santos CIM, Neves MGPMS, Faustino MAF, Tomé AC, Silva AMS, Paz FAA, Cavaleiro JAS (2009) Corroles in 1,3-dipolar cycloaddition reactions. J Porphyrins Phthalocyanines 13:358

    CAS  Google Scholar 

  73. Sorasaenee K, Taqavi P, Henling LM, Gray HB, Tkachenko E, Mahammed A, Gross Z (2007) Amphiphilic aluminium(III) and gallium(III) corroles. J Porphyrins Phthalocyanines 11:189

    CAS  Google Scholar 

  74. Santos CIM, Oliveira E, Barata JFB, Faustino MAF, Cavaleiro JAS, Neves MGPMS, Lodeiro C (2012) Corroles as anion chemosensors: exploiting their fluorescence behaviour from solution to solid-supported devices. J Mater Chem 22:13811

    CAS  Google Scholar 

  75. Mastroianni M, Zhu W, Stefanelli M, Nardis S, Fronczek FR, Smith KM, Ou Z, Kadish KM, Paolesse R (2008) β-Nitro derivatives of germanium(IV) corrolates. Inorg Chem 47:11680

    CAS  Google Scholar 

  76. Stefanelli M, Mandoj F, Mastroianni M, Nardis S, Mohite P, Fronczek FR, Smith KM, Kadish KM, Xiao X, Ou Z, Chen P, Paolesse R (2011) Amination reaction on copper and germanium β-nitrocorrolate. Inorg Chem 50:8281

    CAS  Google Scholar 

  77. Pomarico G, Fronczek FR, Nardis S, Smith KM, Paolesse R (2011) Synthetic protocols for the nitration of corroles. J Porphyrins Phthalocyanines 15:1085

    CAS  Google Scholar 

  78. Pomarico G, Xiao X, Nardis S, Paolesse R, Fronczek FR, Smith KM, Fang Y, Ou Z, Kadish KM (2010) Synthesis and characterization of free-base, copper, and nickel isocorroles. Inorg Chem 49:5766

    CAS  Google Scholar 

  79. Stefanelli M, Mastroianni M, Nardis S, Licoccia S, Fronczek FR, Smith KM, Zhu W, Ou Z, Kadish KM, Paolesse R (2007) Functionalization of corroles: the nitration. Inorg Chem 46:10791

    CAS  Google Scholar 

  80. Smith KM, Barnett GH, Evans B, Martynenko Z (1979) Novel meso-substitution reactions of metalloporphyrins. J Am Chem Soc 101:5953

    CAS  Google Scholar 

  81. Stefanelli M, Pomarico G, Tortora L, Nardis S, Fronczek FR, McCandless GT, Smith KM, Manowong M, Fang YC, Kadish KM, Rosa A, Ricciardi G, Paolesse R (2012) β-Nitro-5,10,15-tritolylcorroles. Inorg Chem 51:6928

    CAS  Google Scholar 

  82. Nardis S, Stefanelli M, Mohite P, Pomarico G, Tortora L, Manowong M, Chen P, Kadish KM, Fronczek FR, McCandless GT, Smith KM, Paolesse R (2012) β-Nitro derivatives of iron corrolates. Inorg Chem 51:3910

    CAS  Google Scholar 

  83. Vaz Serra VI, Pires SMG, Alonso CMA, Neves MGPMS, Tomé AC, Cavaleiro JAS (2013) meso-Tetraarylporphyrins bearing nitro or amino groups: synthetic strategies and reactivity profiles. Top Heterocycl Chem 33. doi:10.1007/7081_2013_101

  84. Collman JP, Decréau RA (2005) 5,10,15-Tris(o-aminophenyl) corrole (TAPC) as a versatile synthon for the preparation of corrole-based hemoprotein analogs. Org Lett 7:975

    CAS  Google Scholar 

  85. Collman JP, Kaplun M, Decréau RA (2006) Metal corroles as electrocatalysts for oxygen reduction. Dalton Trans 554

    Google Scholar 

  86. Barbe J-M, Canard G, Brandès S, Guilard R (2005) Organic–inorganic hybrid sol–gel materials incorporating functionalized cobalt(III) corroles for the selective detection of CO. Angew Chem Int Ed 44:3103

    CAS  Google Scholar 

  87. Barbe J-M, Canard G, Brandès S, Guilard R (2005) Synthesis and physicochemical characterization of meso-functionalized corroles: precursors of organic–inorganic hybrid materials. Eur J Org Chem 4601

    Google Scholar 

  88. Barbe J-M, Canard G, Brandès S, Guilard R (2007) Selective chemisorption of carbon monoxide by organic–inorganic hybrid materials incorporating cobalt(III) corroles as sensing components. Chem Eur J 13:2118

    CAS  Google Scholar 

  89. Gao Y, Liu J, Jiang W, Xia M, Zhang W, Li M, Åkermark B, Sun L (2007) Synthesis and photophysical and electrochemical properties of a binuclear Ru(bpy)3-Cu(III) corrole complex. J Porphyrins Phthalocyanines 11:463

    CAS  Google Scholar 

  90. Richeter S, Jeandon C, Ruppert R, Callot HJ (2002) A modular approach to porphyrin oligomers using metal ions as connectors. Chem Commun 266

    Google Scholar 

  91. Richeter S, Hadj-Aïssa A, Taffin C, van der Lee KA, Leclercq D (2007) Synthesis and structural characterisation of the first N-heterocyclic carbene ligand fused to a porphyrin. Chem Commun 2148

    Google Scholar 

  92. Costa JIT, Tomé AC, Neves MGPMS, Cavaleiro JAS (2011) 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin: a versatile platform to novel porphyrinic materials. J Porphyrins Phthalocyanines 15:1117

    Google Scholar 

  93. Aviezer D, Cotton S, David M, Segev A, Khaselev N, Galili N, Gross Z, Yayon A (2000) Porphyrin analogues as novel antagonists of fibroblast growth factor and vascular endothelial growth factor receptor binding that inhibit endothelial cell proliferation, tumor progression, and metastasis. Cancer Res 60:2973

    CAS  Google Scholar 

  94. Hori T, Osuka A (2010) Nucleophilic substitution reactions of meso-5,10,15-tris(pentafluorophenyl)-corrole; synthesis of ABC-type corroles and corrole-based organogels. Eur J Org Chem 2379

    Google Scholar 

  95. Cardote TAF, Barata JFB, Faustino MAF, Preuß A, Neves MGPMS, Cavaleiro JAS, Ramos CIV, Santana-Marques MGO, Röder B (2012) Pentafluorophenylcorrole-d-galactose conjugates. Tetrahedron Lett 53:6388

    CAS  Google Scholar 

  96. Barata JFB, Daniel-da-Silva AL, Neves MGPMS, Cavaleiro JAS, Trindade T (2013) Corrole-silica hybrid particles: synthesis and effects on singlet oxygen generation. RSC Adv 3:274

    CAS  Google Scholar 

  97. Maes W, Ngo TH, Vanderhaeghen J, Dehaen W (2007) Meso-pyrimidinyl-substituted A2B-corroles. Org Lett 9:3165

    CAS  Google Scholar 

  98. Ngo TH, Nastasi F, Puntoriero F, Campagna S, Dehaen W, Maes W (2010) Meso-pyrimidinyl-substituted A2B- and A3-corroles. J Org Chem 75:2127

    CAS  Google Scholar 

  99. Cavaleiro JAS, Tomé AC, Neves MGPMS (2010) Meso-tetraarylporphyrin derivatives: new synthetic methodologies. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science. World Scientific, Singapore

    Google Scholar 

  100. Cavaleiro JAS, Neves MGPMS, Tomé AC (2003) Cycloaddition reactions of porphyrins. Arkivoc: 107

    Google Scholar 

  101. Tomé AC, Neves MGPMS, Cavaleiro JAS (2009) Porphyrins and other pyrrolic macrocycles in cycloaddition reactions. J Porphyrins Phthalocyanines 13:408

    Google Scholar 

  102. Silva AMG, Cavaleiro JAS (2008) Porphyrins in Diels–Alder and 1,3-dipolar cycloaddition reactions. In: Gribble GW, Joule JA (eds) Progress in heterocyclic chemistry, vol 19. Elsevier, Amsterdam, p 44

    Google Scholar 

  103. Barata JFB, Silva AMG, Faustino MAF, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2004) Novel Diels–Alder and thermal [4+4] cycloadditions of corroles. Synlett 7:1291

    Google Scholar 

  104. Barata JFB (2009) Synthesis and reactivity studies of new corrole derivatives. Department of Chemistry, University of Aveiro, Aveiro, p 248

    Google Scholar 

  105. Barata JFB, Silva AMG, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2006) β,β′-Corrole dimers. Tetrahedron Lett 47:8171

    CAS  Google Scholar 

  106. Hiroto S, Furukawa K, Shinokubo H, Osuka A (2006) Synthesis and biradicaloid character of doubly linked corrole dimers. J Am Chem Soc 128:12380

    CAS  Google Scholar 

  107. Li CJ, Fechtel M, Feng YQ, Krautler B (2012) Corroles programmed for regioselective cycloaddition chemistry – synthesis of a bisadduct with C-60-fullerene. J Porphyrins Phthalocyanines 16:556

    CAS  Google Scholar 

  108. Vale LSHP, Barata JFB, Neves MGPMS, Faustino MAF, Tomé AC, Silva AMS, Paz FAA, Cavaleiro JAS (2007) Novel quinone-fused corroles. Tetrahedron Lett 48:8904

    CAS  Google Scholar 

  109. Ramos CIV, Santana-Marques MG, Ferrer-Correia AJ, Barata JFB, Tomé AC, Neves MGPMS, Cavaleiro JAS, Abreu PE, Pereira MM, Pais AACC (2012) Differentiation of aminomethyl corrole isomers by mass spectrometry. J Mass Spectrom 47:516

    CAS  Google Scholar 

  110. D’Souza F, Chitta R, Ohkubo K, Tasior M, Subbaiyan NK, Zandler ME, Rogacki MK, Gryko DT, Fukuzumi S (2008) Corrole-fullerene dyads: formation of long-lived charge-separated states in nonpolar solvents. J Am Chem Soc 130:14263

    Google Scholar 

  111. Lewandowska K, Barszcz B, Wolak J, Graja A, Grzybowski M, Gryko DT (2013) Vibrational properties of new corrole-fullerene dyad and its components. Dyes Pigm 96:249

    CAS  Google Scholar 

  112. Scrivanti A, Beghetto V, Matteoli U, Antonaroli S, Marini A, Mandoj F, Paolesse R, Crociani B (2004) Iminophosphine–palladium(0) complexes as highly active catalysts in the Suzuki reaction. Synthesis of undecaaryl substituted corroles. Tetrahedron Lett 45:5861

    CAS  Google Scholar 

  113. Berg S, Thomas KE, Beavers CM, Ghosh A (2012) Undecaphenylcorroles. Inorg Chem 51:9911

    CAS  Google Scholar 

  114. König M, Reith LM, Monkowius U, Knör G, Bretterbauer K, Schoefberger W (2011) Suzuki–Miyaura cross-coupling reaction on copper-trans-A2B-corroles with excellent functional group tolerance. Tetrahedron 67:4243

    Google Scholar 

  115. Kinzel T, Zhang Y, Buchwald SL (2010) A new palladium precatalyst allows for the fast Suzuki–Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids. J Am Chem Soc 132:14073

    CAS  Google Scholar 

  116. Reith LM, Koenig M, Schwarzinger C, Schoefberger W (2012) BiIII-corroles: a versatile platform for the synthesis of functionalized corroles. Eur J Inorg Chem 4342

    Google Scholar 

  117. Reith LM, Stiftinger M, Monkowius U, Knor G, Schoefberger W (2011) Synthesis and characterization of a stable bismuth(III) A3-corrole. Inorg Chem 50:6788

    CAS  Google Scholar 

  118. Bröring M, Funk M, Milsmann C (2009) Investigating different strategies towards the preparation of chiral and achiral bis-picket fence corroles. J Porphyrins Phthalocyanines 13:107

    Google Scholar 

  119. Nigel-Etinger I, Mahammed A, Gross Z (2011) Covalent versus non-covalent (biocatalytic) approaches for enantioselective sulfoxidation catalyzed by corrole metal complexes. Catal Sci Technol 1:578

    CAS  Google Scholar 

  120. Tasior M, Gryko DT, Shen J, Kadish KM, Becherer T, Langhals H, Ventura B, Flamigni L (2008) Energy- and electron-transfer processes in corrole-perylenebisimide-triphenylamine array. J Phys Chem C 112:19699

    CAS  Google Scholar 

  121. Zhan H-Y, Liu H-Y, Lu J, Wang A-Z, You L-L, Wang H, Ji L-N, Jiang H-F (2010) Alkynyl corroles: synthesis by Sonogashira coupling reaction and the physicochemical properties. J Porphyrins Phthalocyanines 14:150

    CAS  Google Scholar 

  122. Hiroto S, Hisaki I, Shinokubo H, Osuka A (2005) Synthesis of corrole derivatives through regioselective Ir-catalyzed direct borylation. Angew Chem Int Ed 44:6763

    CAS  Google Scholar 

  123. Pomarico G, Nardis S, Paolesse R, Ongayi OC, Courtney BH, Fronczek FR, Vicente MGH (2011) Synthetic routes to 5,10,15-triaryl-tetrabenzocorroles. J Org Chem 76:3765

    CAS  Google Scholar 

Download references

Acknowledgments

Authors are grateful to “Fundação para a Ciência e a Tecnologia – FCT, QREN, FEDER and COMPETE” Lisbon, for funding QOPNA (the Research Unit in Organic Chemistry), CICECO, and research projects. Thanks are also due to FCT for grants awarded to PhD and Post-Doc students. Thanks are also due to the University of Aveiro, to all students involved in the work carried out in Aveiro.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to José A. S. Cavaleiro .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Barata, J.F.B., Santos, C.I.M., Neves, M.G.P.M.S., Faustino, M.A.F., Cavaleiro, J.A.S. (2013). Functionalization of Corroles. In: Paolesse, R. (eds) Synthesis and Modifications of Porphyrinoids. Topics in Heterocyclic Chemistry, vol 33. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2013_107

Download citation

Publish with us

Policies and ethics