Synthesis 2018; 50(14): 2678-2692
DOI: 10.1055/s-0037-1609756
short review
© Georg Thieme Verlag Stuttgart · New York

Carbene-Type Species in the Functionalization of Porphyrin Derivatives

Ana T. P. C. Gomes*
a  Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Email: ana.peixoto@ua.pt
,
Luana da S. M. Forezi*
b  Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, 24020-150 Niterói, RJ, Brazil   Email: luanaforezi@hotmail.com
,
Mário M. Q. Simões
a  Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Email: ana.peixoto@ua.pt
,
Daniel T. Gonzaga
b  Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, 24020-150 Niterói, RJ, Brazil   Email: luanaforezi@hotmail.com
,
Mariana F. C. Cardoso
b  Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, 24020-150 Niterói, RJ, Brazil   Email: luanaforezi@hotmail.com
,
Fernando de C. Da Silva
b  Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, 24020-150 Niterói, RJ, Brazil   Email: luanaforezi@hotmail.com
,
Maria G. P. M. S. Neves
a  Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Email: ana.peixoto@ua.pt
,
Vítor F. Ferreira
c  Departamento de Tecnologia Farmacêutica, Faculdade de Farmácia, Universidade Federal Fluminense, Niterói, RJ, 24241-002, Brazil
,
José A. S. Cavaleiro
a  Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Email: ana.peixoto@ua.pt
› Author Affiliations
Thanks are due to the University of Aveiro, to the ‘Fundação para a Ciência e a Tecnologia’ (FCT), the European Union, QREN, FEDER and COMPETE for funding the QOPNA research unit (project PEst-C/QUI/UI0062/2013) and the Portuguese National NMR Network (RNRMN). A. T. P. C. G. thanks FCT (Portugal) for her research grant (SFRH/BPD/79521/2011). L. S. M. F. thanks CAPES (Brazil); D. T. G. G. and also M. F. C. C. thank FAPERJ (Brazil) for their post-doctoral fellowships. V. F. F. and F. C. S. thank FAPERJ and CNPQ (Brazil) for their research grants.
Further Information

Publication History

Received: 07 March 2018

Accepted after revision: 09 April 2018

Publication Date:
19 June 2018 (online)


Abstract

Carbenes and NHCs play an important role in porphyrin chemistry and several synthetically useful transformations leading to the preparation of new porphyrin derivatives have been developed. This short review presents an overview covering the literature from 2007–2017, on the role of these transient species in the functionalization of porphyrin macrocycles.

 
  • References

  • 1 Geuther A. Hermann M. Justus Liebigs Ann. Chem. 1855; 95: 211
  • 2 de Fremont P. Marion N. Nolan SP. Coord. Chem. Rev. 2009; 253: 862
    • 3a Marion N. Nolan SP. Chem. Soc. Rev. 2008; 37: 1776
    • 3b Marion N. Diez-Gonzalez S. Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 2988
  • 4 Fischer H. Medick H. Justus Liebigs Ann. Chem. 1935; 517: 245
  • 5 Callot HJ. Dalton. Trans. 2008; 6346
  • 6 Gomes A. Neves MG. P. M. S. Cavaleiro JA. S. J. Porphyrins Phthalocyanines 2011; 15: 835
    • 7a Callot HJ. Tetrahedron Lett. 1972; 11: 1011
    • 7b Callot HJ. Bull. Soc. Chim. Fr. 1972; 4387
    • 8a Silva AM. G. Tome AC. Neves MG. P. M. S. Cavaleiro JA. S. Synlett 2002; 1155
    • 8b Gomes A. Leao RA. C. da Silva FC. Neves M. Faustino MA. F. Tome AC. Silva AM. S. Pinheiro S. de Souza M. Ferreira VF. Cavaleiro JA. S. J. Porphyrins Phthalocyanines 2009; 13: 247
    • 8c Gomes AT. P. C. Leao RA. C. Alonso CM. A. Neves MG. P. M. S. Faustino MA. F. Tome AC. Silva AM. S. Pinheiro S. de Souza MC. B. V. Ferreira VF. Cavaleiro JA. S. Helv. Chim. Acta 2008; 91: 2270
  • 10 Gomes A. Faustino MA. F. Neves MG. P. M. S. Ferreira VF. Juarranz A. Cavaleiro JA. S. Sanz-Rodriguez F. RSC Adv. 2015; 5: 33496
    • 11a Cavaleiro JA. S. Gerdan VM. Hombrecher HK. Neves MG. P. M. S. Silva AM. S. Heterocycl. Commun. 1997; 3: 253
    • 11b Hombrecher HK. Gerdan VM. Cavaleiro JA. S. Neves M. Heterocycl. Commun. 1997; 3: 453
  • 12 Kopke T. Pink M. Zaleski JM. Synlett 2006; 2183
  • 13 Kopke T. Zaleski JM. Anti-cancer Agents Med. Chem. 2008; 8: 292
  • 14 Boerner LJ. K. Dye DF. Kopke T. Zaleski JM. Coord. Chem. Rev. 2013; 257: 599
  • 15 Carrie D. Srour H. Le Maux P. Simonneaux G. Tetrahedron Lett. 2016; 57: 1179
    • 16a Hopkinson MN. Richter C. Schedler M. Glorius F. Nature (London) 2014; 510: 485
    • 16b Crabtree RH. Coord. Chem. Rev. 2007; 251: 595
  • 17 Toganoh M. Hihara T. Furuta H. Inorg. Chem. 2010; 49: 8182
  • 18 Richeter S. Hadj-Aissa A. Taffin C. van der Lee A. Leclercq D. Chem. Commun. 2007; 2148
  • 19 Lefebvre JF. Leclercq D. Gisselbrecht JP. Richeter S. Eur J. Org. Chem. 2010; 1912
  • 20 Lefebvre JF. Lo MD. Leclercq D. Richeter S. Chem. Commun. 2011; 47: 2976
  • 21 Lefebvre JF. Lo M. Gisselbrecht JP. Coulembier O. Clement S. Richeter S. Chem. Eur. J. 2013; 19: 15652
  • 22 Lefebvre JF. Longevial JF. Molvinger K. Clement S. Richeter S. C. R. Chim. 2016; 19: 94
  • 23 Longevial JF. Langlois A. Buisson A. Devillers CH. Clement S. van der Lee A. Harvey PD. Richeter S. Organometallics 2016; 35: 663
    • 24a Boselli L. Ader I. Carraz M. Hemmert C. Cuvillier O. Gornitzka H. Eur. J. Med. Chem. 2014; 85: 87
    • 24b Liu WK. Gust R. Chem. Soc. Rev. 2013; 42: 755
  • 25 Longevial J.-F. El Cheikh K. Aggad D. Lebrun A. van der Lee A. Tielens F. Clément S. Morère A. Garcia M. Gary-Bobo M. Richeter S. Chem. Eur. J. 2017; 23: 14017
    • 26a Haumesser J. Gisselbrecht JP. Weiss J. Ruppert R. Chem. Commun. 2012; 48: 11653
    • 26b Haumesser J. Gisselbrecht JP. Karmazin-Brelot L. Bailly C. Weiss J. Ruppert R. Organometallics 2014; 33: 4923
  • 27 Jung C. de Vries S. Schunemann V. Arch. Biochem. Biophys. 2011; 507: 44
  • 28 Wolf CR. Mansuy D. Nastainczyk W. Deutschmann G. Ullrich V. Mol. Pharmacol. 1977; 13: 698
  • 29 Mansuy D. Battioni JP. Chottard JC. Ullrich V. J. Am. Chem. Soc. 1979; 101: 3971
  • 30 Groves JT. Avaria-Neisser GE. Fish KM. Imachi M. Kuczkowski RL. J. Am. Chem. Soc. 1986; 108: 3837
  • 31 Simonneaux G. Le Maux P. Top. Organomet. Chem. 2006; 17: 83
  • 32 Anding BJ. Woo LK. Handbook of Porphyrin Science . Vol. 21. Kadish KM. Guilard R. Smith K. World Scientific Publishing Company; Hackensack NJ: 2012: 145-319
  • 33 Albrecht M. Maji P. Häusl C. Monney A. Müller-Bunz H. Inorg. Chim. Acta 2012; 380: 90
  • 34 Olguin J. Muller-Bunz H. Albrecht M. Chem. Commun. 2014; 50: 3488
  • 35 Chan K.-H. Guan X. Lo VK.-Y. Che C.-M. Angew. Chem. Int. Ed. 2014; 53: 2982
  • 36 Anding BJ. Ellern A. Woo LK. Organometallics 2014; 33: 2219
  • 37 Boschi T. Licoccia S. Paolesse R. Tagliatesta P. Pelizzi G. Vitali F. Organometallics 1989; 8: 330
  • 38 Liu YL. Xu W. Zhang J. Fuller W. Schulz CE. Li JF. J. Am. Chem. Soc. 2017; 139: 5023