Regioselective synthesis of multifunctionalised porphyrins - Coupling of mono-(pentafluorophenyl)porphyrins to electrophiles

Authors
Shaw, SJ Edwards, C Boyle, RW
Citation
Sj. Shaw et al., Regioselective synthesis of multifunctionalised porphyrins - Coupling of mono-(pentafluorophenyl)porphyrins to electrophiles, TETRAHEDR L, 40(42), 1999, pp. 7585-7586
Citations number
5
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
42
Year of publication
1999
Pages
7585 - 7586
Database
ISI
SICI code
0040-4039(19991015)40:42<7585:RSOMP->2.0.ZU;2-I
Abstract
A method is presented for the coupling of meso-phenylporphyrins, bearing a single pentafluorophenyl ring, to electrophilic moieties. Selective displac ement of the para fluorine atom, using sodium sulphide, results in a transi ent thiolate species capable of reacting with electrophiles to give a thioe ther link. A wide range of electrophiles can be used including alkyl iodide s, epoxides and activated aromatic systems. (C) 1999 Elsevier Science Ltd. All rights reserved.