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.
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
subject category
Chemistry
authors
Gomes, ATPC; Freire, PC; Domingos, CRM; Neves, MGPMS; Cavaleiro, JAS; Paz, FAA; Saraiva, JA; Tome, AC
our authors
Filipe Alexandre Almeida Paz
Principal Researcheracknowledgements
Thanks are due to University of Aveiro and FCT/MEC for the financial support to the project PTDC/QEQ-QOR/1273/2012 and the QOPNA research project (FCT UID/QUI/00062/2013) through national funds and where applicable co-financed by the FEDER, within the PT2020 Partnership Agreement, and also to the Portuguese NMR Network. Part of this work was developed within the scope of the project CICECO-Aveiro Institute of Materials, POCI-01-0145-FEDER-007679 (FCT Ref. UID/CTM/50011/2013), financed by national funds through the FCT/MEC and when appropriate co-financed by FEDER under the PT2020 Partnership Agreement. We also wish to thank CICECO for specific funding towards the purchase of the single-crystal X-ray diffractometer. Ana Gomes thanks FCT for her post-doctoral grant (SFRH/BPD/79521/2011).