World Scientific
  • Search
  •   
Skip main navigation

Cookies Notification

We use cookies on this site to enhance your user experience. By continuing to browse the site, you consent to the use of our cookies. Learn More
×
Our website is made possible by displaying certain online content using javascript.
In order to view the full content, please disable your ad blocker or whitelist our website www.worldscientific.com.

System Upgrade on Tue, Oct 25th, 2022 at 2am (EDT)

Existing users will be able to log into the site and access content. However, E-commerce and registration of new users may not be available for up to 12 hours.
For online purchase, please visit us again. Contact us at [email protected] for any enquiries.

The evolution of corrole synthesis — from simple one-pot strategies to sophisticated ABC-corroles

    https://doi.org/10.1142/S1088424616300056Cited by:17 (Source: Crossref)

    This review highlights synthesis procedures to obtain A3-, cis- and trans- A2B- and ABC-corroles. Synthesis methods from the early beginning of “corrole chemistry”, acid-catalyzed condensation methods of various building blocks (pyrrole, aldehyde, dipyrromethane, dipyrromethane-carbinol, and dipyrromethane-dicarbinol etc.), possible side reaction during Brønsted acid catalyzed reactions (scrambling), one-pot synthesis of corroles, and post-macrocyclization modification reactions of meso-substituted A3-corroles are discussed.

    Dedicated to Professor Kevin M. Smith on the occasion of his 70th birthday

    References

    • 1. Vicente MdG and Smith KM. Curr. Org. Syn. 2014; 11: 3–28. Crossref, ISIGoogle Scholar
    • 2. Eschenmoser A. Angew. Chem. Int. Ed. Engl. 1988; 27: 5–39. Crossref, ISIGoogle Scholar
    • 3. Moss GP. Eur. J. Biochem. 1988; 178: 277–328. CrossrefGoogle Scholar
    • 4. Gryko DT. J. Porphyrins Phthalocyanines 2008; 12: 906–917. Link, ISIGoogle Scholar
    • 5. Johnson AW and Kay IT. Proc. Chem. Soc 1964; 89–90. Google Scholar
    • 6. Conlon M, Johnson AW, Overend WR, Rajapaksa D and Elson CM. J. Chem. Soc., Perkin Trans. 1973; 1: 2281–2288. CrossrefGoogle Scholar
    • 7. Paolesse R, Licoccia S, Fanciullo M, Morgante E and Boschi T. Inorg. Chim. Acta 1993; 203: 107–114. Crossref, ISIGoogle Scholar
    • 8. Paolesse R, Licoccia S, Bandoli G, Dolmella A and Boschi T. Inorg. Chem. 1994; 33: 1171–1176. Crossref, ISIGoogle Scholar
    • 9. Kin Tse M, Zhang Z and Shing Chan K. Chem. Commun. 1998; 11: 1199–1200. Google Scholar
    • 10. Gross Z, Galili N and Saltsman I. Angew. Chem. Int. Ed. 1999; 38: 1427–1429. Crossref, ISIGoogle Scholar
    • 11. Paolesse R, Mini S, Sagone F, Boschi T, Jaquinod L, Nurco DJ and Smith KM. Chem. Commun. 1999; 14: 1307–1308. Crossref, ISIGoogle Scholar
    • 12. Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J and Korsakoff L. J. Org. Chem. 1967; 32: 476. Crossref, ISIGoogle Scholar
    • 13. Lindsey JS, Schreiman IC, Hsu HC, Kearney PC and Marguerettaz AM. J. Org. Chem. 1987; 52: 827–836. Crossref, ISIGoogle Scholar
    • 14. Lindsey JS. In The Porphyrin Handbook, Vol. 1, Kadish KMSmith KMGuilard R. (Eds.) Academic Press: 1999. Google Scholar
    • 15. Jae-Won Ka, Won-Seob Cho and Chang-Hee Lee. Tetrahedron Lett. 2000; 41: 8121–8125. Crossref, ISIGoogle Scholar
    • 16. Briñas RP and Brückner C. Synlett 2001; 3: 442–444. CrossrefGoogle Scholar
    • 17. Paolesse R, Nardis S, Sagone F and Khoury RG. J. Org. Chem. 2001; 66: 550–556. Crossref, ISIGoogle Scholar
    • 18. Nardis S, Monti D and Paolesse R. Mini-Rev. Org. Chem. 2005; 2: 355–374. Crossref, ISIGoogle Scholar
    • 19. Jae-Won Ka and Chang-Hee Lee. Tetrahedron Lett. 2000; 41: 4609–4613. Crossref, ISIGoogle Scholar
    • 20. Asokan C, Smeets S and Dehaen W. Tetrahedron Lett. 2001; 42: 4483–4485. Crossref, ISIGoogle Scholar
    • 21. Gryko DT and Jadach K. J. Org. Chem. 2001; 66: 4267–4275. Crossref, ISIGoogle Scholar
    • 22. Littler BJ, Ciringh Y and Lindsey JS. J. Org. Chem. 1999; 64: 2864–2872. Crossref, ISIGoogle Scholar
    • 23. Gryko DT and Koszarna B. Org. Biomol. Chem. 2003; 1: 350–357. Crossref, ISIGoogle Scholar
    • 24. Gryko DT and Koszarna B. Synthesis 2004; 13: 2205–2209. Crossref, ISIGoogle Scholar
    • 25. Koszarna B and Gryko DT. J. Org. Chem. 2006; 71: 3707–3717. Crossref, ISIGoogle Scholar
    • 26. Král V, Vašek P and Dolensky B. Collect. Czech. Chem. Commun. 2004; 69: 1126–1136. CrossrefGoogle Scholar
    • 27. Ooi S, Tanaka T and Osuka A. Eur. J. Org. Chem. 2015; 2015: 130–134. Crossref, ISIGoogle Scholar
    • 28. Ooi S, Yoneda T, Tanaka T and Osuka A. Chem. Eur. J. 2015; 21: 7772–7779. Crossref, ISIGoogle Scholar
    • 29. Guilard R, Gryko DT, Canard G, Barbe J, Koszarna B, Brandès S and Tasior M. Org. Lett. 2002; 4: 4491–4494. Crossref, ISIGoogle Scholar
    • 30. Richard A Decréau and James P Collman. Tetrahedron Lett. 2003; 44: 3323–3327. Crossref, ISIGoogle Scholar
    • 31. Gryko DT, Tasior M and Koszarna B. J. Porphyrins Phthalocyanines 2003; 7: 239–248. Link, ISIGoogle Scholar
    • 32. Rao PD, Littler BJ, Geier GR and Lindsey JS. J. Org. Chem. 2000; 65: 1084–1092. Crossref, ISIGoogle Scholar
    • 33. Kadish KM, Han BC, Franzen MM and Araullo-McAdams C. J. Am. Chem. Soc. 1990; 112: 8364–8368. Crossref, ISIGoogle Scholar
    • 34. Samaroo D, Vinodu M, Chen X and Drain CM. J. Comb. Chem. 2007; 9: 998–1011. Crossref, ISIGoogle Scholar
    • 35. Costa JI, Tomé AC, Neves MG and Cavaleiro JA. J. Porphyrins Phthalocyanines 2011; 15: 1116–1133. Link, ISIGoogle Scholar
    • 36. Barata J, Santos C, Neves M, Faustino M and Cavaleiro J. In Functionalization of Corroles. Synthesis and Modifications of Porphyrinoids, Vol. 33, Paolesse R. (Ed.) Topics in Heterocyclic Chemistry; Springer Berlin Heidelberg: 2014; pp. 79–141. Google Scholar
    • 37. Avieza D, Cotton S, David M, Segev A, Khaselev N, Galili N, Gross Z and Yayon A. Cancer Res. 2000; 60: 2973–2980. ISIGoogle Scholar
    • 38. Hori T and Osuka A. Eur. J. Org. Chem. 2010; 12: 2379–2386. Crossref, ISIGoogle Scholar
    • 39. Cardote TA, Barata JF, Faustino MAF, Preuß A, Neves, Graça MPMS, Cavaleiro JA, Ramos CI, Santana-Marques, Graça MO and Röder B. Tetrahedron Lett. 2012; 53: 6388–6393. Crossref, ISIGoogle Scholar
    • 40. Reith LM, Stiftinger M, Monkowius U, Knör G and Schoefberger W. Inorg. Chem. 2011; 50: 6788–6797. Crossref, ISIGoogle Scholar
    • 41. Reith LM, Koenig M, Schwarzinger C and Schoefberger W. Eur. J. Inorg. Chem. 2012; 27: 4342–4349. Crossref, ISIGoogle Scholar
    • 42. Schmidlehner M, Faschinger F, Reith LM, Ertl M and Schoefberger W. Appl. Organometal. Chem. 2013; 27: 395–405. Crossref, ISIGoogle Scholar
    • 43. Brückner C, Barta CA, Briñas RP and Krause Bauer JA. Inorg. Chem. 2003; 42: 1673–1680. Crossref, ISIGoogle Scholar
    • 44. Ngo TH, van Rossom W, Dehaen W and Maes W. Org. Biomol. Chem. 2009; 7: 439–443. Crossref, ISIGoogle Scholar
    • 45. Mandoj F, Nardis S, Pomarico G and Paolesse R. J. Porphyrins Phthalocyanines 2008; 12: 19–26. Link, ISIGoogle Scholar
    • 46. Capar C, Thomas KE and Ghosh A. J. Porphyrins Phthalocyanines 2008; 12: 964–967. Link, ISIGoogle Scholar
    • 47. Mahmood MHR, Liu Z, Liu H, Zou H and Chang C. Chin. Chem. Lett. 2014; 25: 1349–1353. Crossref, ISIGoogle Scholar
    • 48. Zhan H, Liu H, Chen H and Jiang H. Tetrahedron Lett. 2009; 50: 2196–2199. Crossref, ISIGoogle Scholar
    • 49. Ma H, Zhang M, Zhang D, Huang R, Zhao Y, Yang H, Liu Y, Weng X, Zhou Y, Deng M, Xu L and Zhou X. Chem. Asian J. 2010; 5: 114–122. Crossref, ISIGoogle Scholar
    • 50. Saltsman I, Botoshansky M and Gross Z. Tetrahedron Lett. 2008; 49: 4163–4166. Crossref, ISIGoogle Scholar
    • 51. Saltsman I, Goldberg I and Gross Z. Org. Lett. 2015; 17: 3214–3217. Crossref, ISIGoogle Scholar
    • 52. Ghosh A and Steene E. J. Biol. Inorg. Chem. 2001; 6: 739–752. Crossref, ISIGoogle Scholar
    Most comprehensive & up-to-date research on PORPHYRINS
    Handbook of Porphyrin Science now available in 46 volumes