Synthesis under high hydrostatic pressure-a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins

Ana T.P.C. Gomes; Patrícia C. Freire; Catarina R.M. Domingos; Maria G.P.M.S. Neves; José A.S. Cavaleiro; Filipe A. Almeida Paz; Jorge A. Saraiva; Augusto C. Tomé

doi:10.1142/S108842461650111X

Synthesis under high hydrostatic pressure-a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins

Ana T.P.C. Gomes, Patrícia C. Freire, Catarina R.M. Domingos, Maria G.P.M.S. Neves, José A.S. Cavaleiro, Filipe A. Almeida Paz, Jorge A. Saraiva, Augusto C. Tomé^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin reacts with primary alkylamines and heterocyclic amines, at 50°C and under high pressure (450 MPa), to produce the N-substituted tetraamino derivatives in high yields. Under similar conditions, the reaction with the bulky dibutylamine and dipentylamine affords the corresponding mono-substituted dialkylaminoporphyrins in 10% yield. This new protocol arises as a considerable improvement of the methods already known, which usually require high temperatures and are not effective when using secondary amines having long alkyl groups.

Original language	English
Pages (from-to)	1377-1389
Number of pages	13
Journal	Journal of Porphyrins and Phthalocyanines
Volume	20
Issue number	8-11
DOIs	https://doi.org/10.1142/S108842461650111X
Publication status	Published - 1 Nov 2016
Externally published	Yes

Keywords

High pressure
Nucleophilic aromatic substitution
Pentafluorophenyl groups
Porphyrins
Primary amines
Secondary amines

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10.1142/S108842461650111X

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Gomes, A. T. P. C., Freire, P. C., Domingos, C. R. M., Neves, M. G. P. M. S., Cavaleiro, J. A. S., Almeida Paz, F. A., Saraiva, J. A., & Tomé, A. C. (2016). Synthesis under high hydrostatic pressure-a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins. Journal of Porphyrins and Phthalocyanines, 20(8-11), 1377-1389. https://doi.org/10.1142/S108842461650111X

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title = "Synthesis under high hydrostatic pressure-a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins",

abstract = "5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin reacts with primary alkylamines and heterocyclic amines, at 50°C and under high pressure (450 MPa), to produce the N-substituted tetraamino derivatives in high yields. Under similar conditions, the reaction with the bulky dibutylamine and dipentylamine affords the corresponding mono-substituted dialkylaminoporphyrins in 10% yield. This new protocol arises as a considerable improvement of the methods already known, which usually require high temperatures and are not effective when using secondary amines having long alkyl groups.",

keywords = "High pressure, Nucleophilic aromatic substitution, Pentafluorophenyl groups, Porphyrins, Primary amines, Secondary amines",

author = "Gomes, {Ana T.P.C.} and Freire, {Patr{\'i}cia C.} and Domingos, {Catarina R.M.} and Neves, {Maria G.P.M.S.} and Cavaleiro, {Jos{\'e} A.S.} and {Almeida Paz}, {Filipe A.} and Saraiva, {Jorge A.} and Tom{\'e}, {Augusto C.}",

note = "Publisher Copyright: {\textcopyright} 2016 World Scientific Publishing Company.",

year = "2016",

month = nov,

day = "1",

doi = "10.1142/S108842461650111X",

language = "English",

volume = "20",

pages = "1377--1389",

journal = "Journal of Porphyrins and Phthalocyanines",

issn = "1088-4246",

publisher = "World Scientific",

number = "8-11",

}

Gomes, ATPC, Freire, PC, Domingos, CRM, Neves, MGPMS, Cavaleiro, JAS, Almeida Paz, FA, Saraiva, JA & Tomé, AC 2016, 'Synthesis under high hydrostatic pressure-a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins', Journal of Porphyrins and Phthalocyanines, vol. 20, no. 8-11, pp. 1377-1389. https://doi.org/10.1142/S108842461650111X

Synthesis under high hydrostatic pressure-a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins. / Gomes, Ana T.P.C.; Freire, Patrícia C.; Domingos, Catarina R.M. et al.
In: Journal of Porphyrins and Phthalocyanines, Vol. 20, No. 8-11, 01.11.2016, p. 1377-1389.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis under high hydrostatic pressure-a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins

AU - Gomes, Ana T.P.C.

AU - Freire, Patrícia C.

AU - Domingos, Catarina R.M.

AU - Neves, Maria G.P.M.S.

AU - Cavaleiro, José A.S.

AU - Almeida Paz, Filipe A.

AU - Saraiva, Jorge A.

AU - Tomé, Augusto C.

PY - 2016/11/1

Y1 - 2016/11/1

N2 - 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin reacts with primary alkylamines and heterocyclic amines, at 50°C and under high pressure (450 MPa), to produce the N-substituted tetraamino derivatives in high yields. Under similar conditions, the reaction with the bulky dibutylamine and dipentylamine affords the corresponding mono-substituted dialkylaminoporphyrins in 10% yield. This new protocol arises as a considerable improvement of the methods already known, which usually require high temperatures and are not effective when using secondary amines having long alkyl groups.

AB - 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin reacts with primary alkylamines and heterocyclic amines, at 50°C and under high pressure (450 MPa), to produce the N-substituted tetraamino derivatives in high yields. Under similar conditions, the reaction with the bulky dibutylamine and dipentylamine affords the corresponding mono-substituted dialkylaminoporphyrins in 10% yield. This new protocol arises as a considerable improvement of the methods already known, which usually require high temperatures and are not effective when using secondary amines having long alkyl groups.

KW - High pressure

KW - Nucleophilic aromatic substitution

KW - Pentafluorophenyl groups

KW - Porphyrins

KW - Primary amines

KW - Secondary amines

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VL - 20

SP - 1377

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JO - Journal of Porphyrins and Phthalocyanines

JF - Journal of Porphyrins and Phthalocyanines

IS - 8-11

ER -

Synthesis under high hydrostatic pressure-a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins

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Keywords

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