Bismuth A₃-Corroles: Useful Precursors for the Development of meso-Substituted Free-Base Corroles

Dedicated to Prof. Dr. Heinz Falk on the occasion of his 75^th birthday

Abstract

Systematic studies on regioselective functionalization reactions employing oxygen-, nitrogen-, and sulfur-containing nucleophiles with bismuth A₃-corroles under the influence of a strong non-nucleophilic base are reported. In the case of the thiols and dithiols a high-yielding reaction procedure was established to obtain mono-, di-, and tri-functionalized corroles at room temperature within short reaction times. The described method offers a possibility to attach bifunctional linker molecules to the para-position of the meso-pentafluorophenyl groups at positions 5, 10, and 15 of the corrole macrocycle. The described reaction strategy may serve as a versatile protocol for the covalent binding of corroles to proteins or antibodies and may be utilized to attach corroles on, for example, gold or titanium surfaces to study surface-supported reactions.

Key words

corrole - bismuth - nucleophiles - regioselective - S_NAr reaction

• References

• 1a Johnson AW, Kay IT. Proc. Chem. Soc. 1964; 89
• 1b Johnson AW, Kay IT. J. Chem. Soc. 1965; 1620
• 2 Aviv-Harel I, Gross Z. Coord. Chem. Rev. 2011; 255: 717
• 3a Gross Z, Simkhovich L, Galili N. Chem. Commun. 1999; 599
• 3b Gross Z, Gray HB. Adv. Synth. Catal. 2004; 346: 165
• 4 Agadjanian H, Ma J, Rentsendorj A, Valluripalli V, Hwang JY, Mahammed A, Farkas DL, Gray HB, Gross Z, Medina-Kauwe LK. Proc. Natl. Acad. Sci. U.S.A. 2009; 106: 6105
• 5 Haber A, Aviram M, Gross Z. Chem. Sci. 2011; 2: 295
• 6 Barbe J.-M, Canard G, Brandès S, Jérôme F, Dubois G, Guilard R. Dalton Trans. 2004; 1208
• 7 Walker D, Chappel S, Mahammed A, Brunschwig BS, Winkler JR, Gray HB, Zaban A, Gross Z. J. Porphyrins Phthalocyanines 2006; 10: 1259
• 8 Gryko DT, Koszarna B. Org. Biomol. Chem. 2003; 1: 350
• 9a Gryko DT, Koszarna B. Synthesis 2004; 2205
• 9b Koszarna B, Gryko DT. J. Org. Chem. 2006; 71: 3707
• 10 Lemon CM, Brothers PJ. J. Porphyrins Phthalocyanines 2011; 15: 809
• 11 Mahammed A, Botoshansky M, Gross Z. Dalton Trans. 2012; 41: 10938
• 12 Golubkov G, Bendix J, Gray HB, Mahammed A, Goldberg I, DiBilio AJ, Gross Z. Angew. Chem. Int. Ed. 2001; 40: 2132
• 13 Tortora L, Nardis S, Fronczek FR, Smith KM, Paolesse R. Chem. Commun. 2011; 47: 4243
• 14 Saltsman I, Mahammed A, Goldberg I, Tkachenko E, Botoshansky M, Gross Z. J. Am. Chem. Soc. 2002; 124: 7411
• 15 König M, Reith LM, Monkowius U, Knör G, Bretterbauer K, Schoefberger W. Tetrahedron 2011; 67: 4243
• 16 Ngo TH, Puntoriero F, Nastasi F, Robeyns K, van Meervelt L, Campagna S, Dehaen W, Maes W. Chem. Eur. J. 2010; 16: 5691
• 17 Ngo TH, Nastasi F, Puntoriero F, Campagna S, Dehaen W, Maes W. J. Org. Chem. 2010; 75: 2127
• 18 Tasior M, Voloshchuk R, Poronik YM, Rowicki T, Gryko DT. J. Porphyrins Phthalocyanines 2011; 15: 1011
• 19 Kadish KM, Han BC, Franzen MM, Araullo-McAdams C. J. Am. Chem. Soc. 1990; 112: 8364
• 20 Samaroo D, Vinodu M, Chen X, Drain CM. J. Comb. Chem. 2007; 9: 998
• 21 Costa JI, Tomé AC, Neves MG, Cavaleiro JA. J. Porphyrins Phthalocyanines 2011; 15: 1116
• 22 Hori T, Osuka A. Eur. J. Org. Chem. 2010; 2379
• 23 Barata JF. B, Santos CI. M, Neves M, Graça PM. S, Faustino MA. F, Cavaleiro JA. S. Functionalization of Corroles . In Topics in Heterocyclic Chemistry . Vol. 33. Paolesse R. Springer; Berlin: 2014: 79-141
• 24 Avieza D, Cotton S, David M, Segev A, Khaselev N, Galili N, Gross Z, Yayon A. Cancer Res. 2000; 2973
• 25 Gross Z, Galili N, Saltsman I. Angew. Chem. Int. Ed. 1999; 38: 1427
• 26 Cardote TA, Barata JF, Faustino MA. F, Preuß A, Neves M, Graça PM. S, Cavaleiro JA, Ramos CI, Santana-Marques M, Graça O, Röder B. Tetrahedron Lett. 2012; 53: 6388
• 27 Reith LM, Stiftinger M, Monkowius U, Knör G, Schoefberger W. Inorg. Chem. 2011; 50: 6788
• 28 Reith LM, Koenig M, Schwarzinger C, Schoefberger W. Eur. J. Inorg. Chem. 2012; 4342
• 29 Schmidlehner M, Faschinger F, Reith LM, Ertl M, Schoefberger W. Appl. Organomet. Chem. 2013; 27: 395
• 30a Ngo TH, van Rossom W, Dehaen W, Maes W. Org. Biomol. Chem. 2009; 7: 439
• 30b Stefanelli M, Shen J, Zhu W, Mastroianni M, Mandoj F, Nardis S, Ou Z, Kadish KM, Fronczek FR, Smith KM, Paolesse R. Inorg. Chem. 2009; 48: 6879
• 31a Timerbaev AR, Hartinger CG, Aleksenko SS, Keppler BK. Chem. Rev. 2006; 106: 2224
• 31b Warnecke A, Fichtner I, Garmann D, Jaehde U, Kratz F. Bioconjugate Chem. 2004; 15: 1349
• 32 Vehkamäki M, Hatanää T, Ritala M, Leskelä M. J. Mater. Chem. 2004; 14: 3191
• 33 Ikeda M, Ochi R, Kurita Y.-s, Pochan DJ, Hamachi I. Chem. Eur. J. 2012; 18: 13091
• 34a Li G, Sproviero EM, McNamara WR, Snoeberger III RC, Crabtree RH, Brudvig GW, Batista VS. J. Phys. Chem. B 2010; 114: 14214
• 34b Li G, Sproviero EM, Snoeberger III RC, Iguchi N, Blakemore JD, Crabtree RH, Brudvig GW, Batista VS. Energy Environ. Sci. 2009; 2: 230
• 34c Kärkäs MD, Johnston EV, Verho O, Åkermark B. Acc. Chem. Res. 2014; 47: 100
• 35 Errington RJ, Fisher GA, Moenadar I, Norman NC. Inorg. Synth. 1997; 31: 98