Synthesis under high hydrostatic pressure - a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins
authors Gomes, ATPC; Freire, PC; Domingos, CRM; Neves, MGPMS; Cavaleiro, JAS; Paz, FAA; Saraiva, JA; Tome, AC
nationality International
journal JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
author keywords porphyrins; nucleophilic aromatic substitution; high pressure; pentafluorophenyl groups; primary amines; secondary amines
keywords 1,3-DIPOLAR CYCLOADDITION REACTIONS; DIELS-ALDER REACTIONS; AROMATIC NUCLEOPHILIC SUBSTITUTION; BARRELENE-FUSED CHLORINS; PORPHYRIN DERIVATIVES; MESO-TETRAARYLPORPHYRINS; AZOMETHINE YLIDES; ORGANIC-SYNTHESIS; CATALYSTS; BACTERIOCHLORINS
abstract 5,10,15,20-Tetrakis(pentafluorophenyl) porphyrin reacts with primary alkylamines and heterocyclic amines, at 50 degrees 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.
publisher WORLD SCI PUBL CO INC
issn 1088-4246
year published 2016
volume 20
issue 08-Nov
beginning page 1377
ending page 1389
digital object identifier (doi) 10.1142/S108842461650111X
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000390248600055
  ciceco authors
  impact metrics
journal analysis (jcr 2017):
journal impact factor 1.217
5 year journal impact factor 1.186
category normalized journal impact factor percentile 28.947
dimensions (citation analysis):
altmetrics (social interaction):



 


Apoio

1suponsers_list_ciceco.jpg