Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2008(1): 1-20
DOI: 10.1055/s-2007-1000823
DOI: 10.1055/s-2007-1000823
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Functionalisation of Phthalocyanines and Subphthalocyanines by Transition-Metal-Catalysed Reactions
Further Information
Received
19 September 2007
Publication Date:
11 December 2007 (online)
Publication History
Publication Date:
11 December 2007 (online)
Abstract
The functionalisation of phthalocyanines and subphthalocyanines by transition-metal-catalysed reactions is reviewed.
1 Introduction
2 Transition-metal-mediated cross-coupling reactions
2.1 Iodophthalocyanine and subphthalocyanine precursors
2.2 Alkynyl-substituted phthalocyanines and subphthalocyanines
2.3 Alkenyl-substituted phthalocyanines and subphthalocyanines
2.4 Aryl-substituted phthalocyanines and subphthalocyanines
2.5 Introduction of heteroatomic substituents in phthalocyanines and subphthalocyanines
3 Conclusions
Key words
phthalocyanines - subphthalocyanines - transition metals - cross-coupling reactions - palladium
-
1a
de la Torre G.Claessens CG.Torres T. Chem. Commun. 2007, 2000 -
1b
Phthalocyanines: Properties and Applications
Vols. 1-4:
Leznoff CC.Lever ABP. VCH; Weinheim: 1989, 1993, 1996. -
1c
The Porphyrin Handbook
Vols. 15-20:
Kadish KM.Smith KM.Guilard R. Academic Press; San Diego: 2003. -
1d
McKeown NB. In Phthalocyanine Materials: Synthesis, Structure and Function Cambridge University Press; Cambridge UK: 1998. -
2a
de la Torre G.Torres T.Agulló-López F. Adv. Mater. 1997, 9: 265 -
2b
de la Torre G.Vázquez P.Agulló-López F.Torres T. J. Mater. Chem. 1998, 8: 1671 -
2c
de la Torre G.Vázquez P.Agulló-López F.Torres T. Chem. Rev. 2004, 104: 3723 -
2d
Loi MA.Neugebauer H.Denk P.Brabec CJ.Sariciftci NS.Gouloumis A.Vázquez P.Torres T. J. Mater. Chem. 2003, 13: 700 -
2e
Guldi DM.Gouloumis A.Vázquez P.Torres T.Georgakilas V.Prato M. J. Am. Chem. Soc. 2005, 127: 5811 -
3a
Torres T.Gouloumis A.Sánchez-Garcia D.Jayawickramarajah J.Seitz W.Guldi DM.Sessler JL. Chem. Commun. 2007, 292 -
3b
Ballesteros B.de la Torre G.Ehli C.Rahman GMA.Agulló-Rueda F.Guldi DM.Torres T. J. Am. Chem. Soc. 2007, 129: 5061 -
3c
Morandeira A.López-Duarte I.Martínez-Díaz MV.O’Regan B.Shuttle C.Haji-Zainulabidin NA.Torres T.Palomares E.Durrant JR. J. Am. Chem. Soc. 2007, 129: 9250 - 4
de la Torre G.Claessens CG.Torres T. Eur. J. Org. Chem. 2000, 2821 -
5a
Claessens CG.González-Rodríguez D.Torres T. Chem. Rev. 2002, 102: 835 -
5b
Torres T. Angew. Chem. Int. Ed. 2006, 45: 961 -
5c
Kobayashi N. In The Porphyrin Handbook Vol. 15:Kadish KM.Smith KM.Guilard R. Academic Press; San Diego: 2003. p.161 -
6a
Sastre A.Torres T.Díaz-Garcia MA.Agulló-López F.Dhenaut C.Brasselet S.Ledoux I.Zyss J. J. Am. Chem. Soc. 1996, 118: 2746 -
6b
del Rey B.Keller U.Torres T.Rojo G.Agulló-López F.Nonell S.Marti C.Brasselet S.Ledoux I.Zyss J. J. Am. Chem. Soc. 1998, 120: 12808 -
6c
Claessens CG.González-Rodríguez D.Torres T.Martín G.Agulló-López F.Ledoux I.Zyss J.Ferro VR.García de la Vega JM. J. Phys. Chem. B 2005, 109: 3800 -
7a
González-Rodríguez D.Torres T.Guldi DM.Rivera J.Herranz MA.Echegoyen L. J. Am. Chem. Soc. 2004, 126: 6301 -
7b
González-Rodríguez D.Claessens CG.Torres T.Liu S.Echegoyen L.Vila S.Nonell N. Chem. Eur. J. 2005, 11: 3881 -
7c
González-Rodríguez D.Torres T.Olmstead MM.Rivera J.Herranz MA.Echegoyen L.Atienza Castellanos C.Guldi DM. J. Am. Chem. Soc. 2006, 128: 10680 - 8
Sharman WM.van Lier JE. In The Porphyrin Handbook Vol. 15:Kadish KM.Smith KM.Guilards R. Academic Press; San Diego: 2003. p.1-59 -
9a
de la Torre G.Torres T. J. Porphyrins Phthalocyanines 1997, 1: 221 -
9b
Torres T.de la Torre G.Garcia-Ruiz J. Eur. J. Org. Chem. 1999, 2323 - 10
González-Cabello A.Vázquez P.Torres T. J. Organomet. Chem. 2001, 637-639: 751 - 11
González-Cabello A.Vázquez P.Torres T.Guldi DM. J. Org. Chem. 2003, 68: 8635 - 12
Sharman WM.van Lier JE. J. Porphyrins Phthalocyanines 2000, 4: 441 - 13
Ali H.van Lier JE. Tetrahedron Lett. 1997, 38: 1157 - 14
Maya EM.Vázquez P.Torres T. Chem. Commun. 1997, 1175 - 15
García-Frutos EM.Díaz DD.Vázquez P.Torres T. Synlett 2006, 3231 - 16
Tian M.Wada T.Kimura-Suda H.Sasabe H. J. Mater. Chem. 1997, 7: 861 - 17
Maya EM.García C.García-Frutos EM.Vázquez P.Torres T. J. Org. Chem. 2000, 65: 2733 - 18
García-Frutos EM.Fernández-Lázaro F.Maya EM.Vázquez P.Torres T. J. Org. Chem. 2000, 65: 6841 - 19
Ali H.St-Jean O.Tremblay-Morin J.-P.van Lier JE. Tetrahedron Lett. 2006, 47: 8275 - 20
Claessens CG.Torres T. Tetrahedron Lett. 2000, 41: 6361 - 21
Claessens CG.Torres T. Chem. Eur. J. 2000, 6: 2168 - 22
Bottari G.Díaz DD.Torres T. J. Porphyrins Phthalocyanines 2006, 10: 1083 - 23
Jiménez AJ.Spanig F.Rodríguez-Morgade MS.Ohkubo K.Fukuzumi S.Guldi DM.Torres T. Org. Lett. 2007, 9: 2481 - 24
García-Frutos EM.Bottari G.Vázquez P.Barberá J.Torres T. Chem. Commun. 2006, 3107 - 25
Claessens CG.Torres T. Chem. Commun. 2004, 1298 - 26
Jeffery T. Tetrahedron 1996, 52: 10113 - 27
Gouloumis A.Liu S.-G.Sastre A.Vázquez P.Echegoyen L.Torres T. Chem. Eur. J. 2000, 6: 3600 - 28
Gouloumis A.González-Rodríguez D.Vázquez P.Torres T.Liu S.Echegoyen L.Ramey J.Hug GL.Guldi DM. J. Am. Chem. Soc. 2006, 128: 12674 - 29
de la Escosura A.Martínez-Díaz MV.Guldi DM.Torres T. J. Am. Chem. Soc. 2006, 128: 4112 - 30
de la Escosura A.Martínez-Díaz MV.Thordarson P.Rowan AE.Nolte RJM.Torres T. J. Am. Chem. Soc. 2003, 125: 12300 - 31
Quintiliani M.García-Frutos EM.Gouloumis A.Vázquez P.Ledoux-Rak I.Zyss J.Claessens CG.Torres T. Eur. J. Org. Chem. 2005, 3911 - 32
Kimura M.Wada K.Ohta KM.Hanabusa K.Shirai H.Kobayashi N. Macromolecules 2001, 34: 4706 -
33a
Kimura M.Ueki H.Ohta K.Hanabusa K.Shirai H.Kobayashi N. Langmuir 2002, 18: 7683 -
33b
de la Escosura A.Martínez-Díaz MV.Torres T.Grubbs RH.Guldi DM.Neugebauer H.Winder C.Drees M.Sariciftci NS. Chem. Asian J. 2006, 1: 148 -
34a
Aranyos V.Castaño AM.Grennberg H. Acta Chem. Scand. 1999, 53: 714 -
34b
Kobayashi N.Fukuda T.Ueno K.Ogino H. J. Am. Chem. Soc. 2001, 123: 10740 -
34c
Sugimori T.Okamoto S.Kotoh N.Handa M.Kasuga K. Chem. Lett. 2000, 1200 -
34d
Sugimori T.Torikata M.Nojima J.Tominaka S.Tobikawa K.Handa M.Kasuga K. Inorg. Chem. Commun. 2002, 5: 1031 - 35
Espinet P.Echavarren A. Angew. Chem. Int. Ed. 2004, 43: 4704 - 36
Claessens CG.Torres T. J. Am. Chem. Soc. 2002, 124: 14522 - 37
Bottari G.Torres T. Chem. Commun. 2004, 2668 - 38
Achar BN.Lokesh KS. J. Organomet. Chem. 2004, 689: 3357 - 39
Wolfe JP.Buchwald SL. J. Org. Chem. 2000, 65: 1144 - 40
Tian H.Ali H.van Lier JE. Tetrahedron Lett. 2000, 8435 - 41
Soares ARM.Martínez-Díaz MV.Bruckner A.Pereira AMVM.Tome JPC.Alonso CMA.Faustino MAF.Neves MGPMS.Tome AC.Silva AMS.Cavaleiro JAS.Torres T.Guldi DM. Org. Lett. 2007, 9: 1557 - 42
Balch AL.Olmstead MM. Chem. Rev. 1998, 98: 2123 - 43
de la Torre G.Gouloumis A.Vázquez P.Torres T. Angew. Chem. Int. Ed. 2001, 40: 2895